Use these links to rapidly review the document
TABLE OF CONTENTS

Table of Contents

UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of
the Securities Exchange Act of 1934 (Amendment No.           )

Filed by the Registrant ý
Filed by a Party other than the Registrant o
Check the appropriate box:
o		Preliminary Proxy Statement
o		Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))
o		Definitive Proxy Statement
ý		Definitive Additional Materials
o		Soliciting Material Pursuant to §240.14a-12

 

Telephone and Data Systems, Inc.
(Name of Registrant as Specified In Its Charter)
(Name of Person(s) Filing Proxy Statement, If other than the Registrant)
Payment of Filing Fee (Check the appropriate box):
ý		No fee required.
o		Fee computed on table below per Exchange Act Rules 14a 6(i)(1) and 0-11.
		(1)		Title of each class of securities to which transaction applies:
		(2)		Aggregate number of securities to which transaction applies:
		(3)		Per unit price or other underlying value of transaction computed pursuant to Exchange Act Rule 0 11 (set forth the amount on which the filing fee is calculated and state how it was determined):
		(4)		Proposed maximum aggregate value of transaction:
		(5)		Total fee paid:
o		Fee paid previously with preliminary materials.
o		Check box if any part of the fee is offset as provided by Exchange Act Rule 0-11(a)(2) and identify the filing for which the offsetting fee was paid previously. Identify the previous filing by registration statement number, or the Form or Schedule and the date of its filing.
		(1)		Amount Previously Paid:
		(2)		Form, Schedule or Registration Statement No.:
		(3)		Filing Party:
		(4)		Date Filed:

---

Table of Contents

SUPPLEMENT DATED NOVEMBER 29, 2011 TO PROXY STATEMENT DATED AUGUST 31, 2011

NOTICE OF ADJOURNED SPECIAL MEETING OF SHAREHOLDERS TO BE RECONVENED
ON JANUARY 13, 2012

TELEPHONE AND DATA SYSTEMS, INC. 30 North LaSalle Street, 40th Floor Chicago, Illinois 60602 312-630-1900
		November 29, 2011

Dear Fellow Shareholders:

        This Supplement describes certain changes to proposals included in the Notice of Special Meeting and Proxy Statement dated August 31, 2011, which we refer to as the "Proxy Statement," of Telephone and Data Systems, Inc., which we refer to as "TDS." This Supplement also provides notice of the date of the adjourned Special Meeting at which the revised proposals will be considered, which we refer to as the "Adjourned Special Meeting," and discloses a change to the record date of shareholders entitled to vote on such proposals at the Adjourned Special Meeting. Capitalized terms used but not otherwise defined herein are used as defined in the Proxy Statement.

        The TDS Board believed that the original proposal of a one-to-one reclassification of the Special Common Shares into Common Shares as set forth in the Proxy Statement was appropriate under the circumstances and consistent with precedent transactions. In accordance with good corporate governance principles, the TDS Board conditioned approval of the Share Consolidation upon ratification and approval by a majority of the outstanding Common Shares and Special Common Shares (excluding shares held by the TDS Voting Trust and certain other persons affiliated with TDS), each voting separately as a class. At the Special Meeting of shareholders held on October 6, 2011, TDS did not have sufficient votes from holders of Common Shares to approve the Share Consolidation.

        As a result and after careful consideration and consultation with its advisors, the TDS Board, including all of the independent directors, is now proposing a new reclassification ratio to accomplish the goal of simplifying TDS' capital structure. The TDS Board believes that its new Share Consolidation proposal addresses the concerns raised by certain holders of its Common Shares while at the same time being fair to the holders of the Special Common Shares. The TDS Board believes that the Share Consolidation is highly valuable to TDS' future and that the proposed reclassification of the Special Common Shares as Common Shares and the related proposals described below and in the Proxy Statement are in the best interests of TDS and the holders of each class of its outstanding shares of capital stock. The TDS Board would like the holders of each class of TDS' outstanding shares to recognize, because each separate class has to approve the Share Consolidation, that the Share Consolidation has to be as fair as possible to each class of shares and that no one class can benefit unduly to the detriment of another class.

        Pursuant to the Share Consolidation, as revised, each Special Common Share would be reclassified as one Common Share, each Common Share would be reclassified as 1.087 Common Shares and each Series A Common Share would be reclassified as 1.087 Series A Common Shares. The primary purpose of this change is to recognize the fact that the Common Shares have generally traded at a premium to the Special Common Shares. Based on a review of the historical average premium, the TDS Board determined that the holders of Common Shares should receive 8.7% additional shares as compared to the holders of Special Common Shares in the Share Consolidation. Also, because the Series A Common Shares are convertible into Common Shares on a one-for-one basis, the TDS Board determined that the holders of Series A Common Shares should receive 8.7% additional shares as compared to the holders of Special Common Shares in the Share Consolidation.

        As more fully described in this Supplement, the TDS Board believes the Share Consolidation Amendment as revised offers several potential advantages as compared to other alternatives considered

---

Table of Contents

by the TDS Board. In particular, the revised Share Consolidation Amendment addresses the concerns raised by certain holders of Common Shares by recognizing the historical average trading premium of the Common Shares, results in less dilution of the voting power of the Common Shares in matters other than the election of directors, and increases the total dividends payable to TDS shareholders without reducing the dividends payable to holders of Special Common Shares.

        As disclosed in the Proxy Statement, TDS had scheduled a Special Meeting of shareholders on October 6, 2011 to vote on the proposals described in the Proxy Statement. This meeting was initially adjourned until October 20, 2011, was adjourned again until November 15, 2011, and then was adjourned until further notice. This Supplement provides notice that the Adjourned Special Meeting to vote on the revised proposals will be held on Friday, January 13, 2012, at 11:00 a.m. Chicago time, at the Standard Club, 320 S. Plymouth Court, Chicago, Illinois.

        The Proxy Statement was previously sent to shareholders of record at the close of business on August 18, 2011. Due to the delays resulting from the adjournments of the Special Meeting as well as the changes to the proposals, the TDS Board has determined to change the record date of shareholders that will be entitled to vote at the Adjourned Special Meeting on January 13, 2012. Accordingly, the record date was changed to the close of business on December 9, 2011. Because of the new record date, we are re-circulating the Proxy Statement as well as new proxy cards together with this Supplement. These materials will be distributed to shareholders shortly after the new record date of December 9, 2011 on or about December 12, 2011.

        In evaluating the revised Share Consolidation Amendment, the TDS Board received and considered a revised opinion of Citigroup Global Markets Inc., which we refer to as "Citi," to the effect that, as of the date of the opinion, and based upon and subject to the considerations and limitations set forth therein, Citi's work described in this Supplement and other factors Citi deemed relevant, the reclassification ratio of one new Common Share for each outstanding Special Common Share and 1.087 new Common Shares for each outstanding Common Share was fair, from a financial point of view, to both the holders of Common Shares and the holders of Special Common Shares (solely in their capacity as holders of Common Shares or holders of Special Common Shares, as the case may be, and disregarding any interest any holder of Common Shares or Special Common Shares, as the case may be, may have in any other equity securities of TDS), as described in the enclosed Supplement and in the opinion attached to the enclosed Supplement.

        In addition, the independent directors of TDS were advised by Credit Suisse Securities (USA) LLC, which we refer to as "Credit Suisse," and independent legal counsel in connection with the foregoing changes.

        A copy of the TDS Charter, marked to show the changes that would be made by the Charter Amendments, including the revised Share Consolidation Amendment, is attached hereto as Exhibit A. Exhibit A also highlights revisions to the Charter Amendments made since the date of the Proxy Statement. The primary change from the version that was attached to the Proxy Statement is that Paragraph A.1 of Article IV has been changed to provide that each Special Common Share would be reclassified as one Common Share, each Common Share would be reclassified as 1.087 Common Shares and each Series A Common Share would be reclassified as 1.087 Series A Common Shares.

        Certain clarifying changes are also being proposed to the Vote Amendment, and certain changes are also being proposed to the Incentive Plan Adoption proposal and the Adjournment Proposal, as discussed herein.

        The TDS Board, including the independent directors, has unanimously approved the proposals as revised, believes that the adoption of such proposals is in the best interests of TDS and holders of each class of its outstanding shares of capital stock and unanimously recommends that you vote "FOR" such proposals.

        As a result of the changes to the proposals and the record date, all proxies and broker votes previously submitted will be deemed null and void. YOU MUST SIGN AND RETURN A NEW PROXY CARD OR ATTEND THE ADJOURNED MEETING FOR YOUR VOTE TO BE COUNTED AT THE ADJOURNED SPECIAL MEETING ON JANUARY 13, 2012.

ii

---

Table of Contents

        YOUR PROXY IS VERY IMPORTANT. The trustees of the Voting Trust that holds a majority of the voting power of all shares of capital stock of TDS, which we refer to as the "TDS Voting Trust", have advised TDS that they intend to vote FOR the revised proposals. However, because the TDS Voting Trust and its trustees and beneficiaries have an interest in the implementation of the proposals and related transactions as discussed in this Supplement and the enclosed Proxy Statement, the TDS Board has also determined to voluntarily submit the revised Share Consolidation Amendment and the Vote Amendment for ratification and approval by a majority of the outstanding Common Shares and Special Common Shares (excluding shares held by the TDS Voting Trust and certain other persons affiliated with TDS), each voting separately as a class. Accordingly, please sign and mail your proxy in the enclosed self-addressed envelope or vote by proxy on the Internet or by phone in accordance with the instructions set forth on the proxy card(s).

        YOU SHOULD NOT RETURN CERTIFICATES WITH THE ENCLOSED PROXY CARD AND YOU SHOULD RETAIN ALL CERTIFICATES WHICH REPRESENT TDS SHARES. IF THE PROPOSALS ARE APPROVED AND BECOME EFFECTIVE, SPECIAL COMMON SHARE CERTIFICATES WILL THEREAFTER REPRESENT AN EQUIVALENT NUMBER OF COMMON SHARES. COMMON SHARE CERTIFICATES AND SERIES A COMMON SHARE CERTIFICATES WILL CONTINUE TO REPRESENT THE NUMBER OF COMMON SHARES AND SERIES A COMMON SHARES IDENTIFIED ON THE CERTIFICATES AND, IF THE PROPOSALS ARE APPROVED AND BECOME EFFECTIVE, HOLDERS OF COMMON SHARES WILL ALSO RECEIVE 0.087 ADDITIONAL COMMON SHARES WITH RESPECT TO EACH COMMON SHARE AND CASH IN LIEU OF FRACTIONAL SHARES, AS DESCRIBED BELOW, AND HOLDERS OF SERIES A COMMON SHARES WILL ALSO RECEIVE 0.087 ADDITIONAL SERIES A COMMON SHARES WITH RESPECT TO EACH SERIES A COMMON SHARE AND CASH IN LIEU OF FRACTIONAL SHARES AS A RESULT OF THE SHARE CONSOLIDATION, AS DESCRIBED BELOW.

        If you have any questions, please call TDS' information agent, MacKenzie Partners, Inc., at 1-800-322-2885. We look forward with pleasure to visiting with you at the Adjourned Special Meeting.

Very truly yours,
Walter C.D. Carlson Chairman of the Board		LeRoy T. Carlson, Jr. President and Chief Executive Officer

iii

---

Table of Contents

(This page has been left blank intentionally.)

iv

Table of Contents

TELEPHONE AND DATA SYSTEMS, INC.
SUPPLEMENT DATED NOVEMBER 29, 2011
TO
PROXY STATEMENT DATED AUGUST 31, 2011

        At the Adjourned Special Meeting, shareholders will be asked to vote on the following proposals:

1.

To consider and approve an amendment, which we refer to as the "Share Consolidation Amendment," to the Restated Certificate of Incorporation of TDS, which we refer to as the "TDS Charter," to reclassify each Special Common Share as one Common Share, reclassify (and subdivide) each Common Share as 1.087 Common Shares and reclassify (and subdivide) each Series A Common Share as 1.087 Series A Common Shares, which we refer to as the "Share Consolidation," and to also add 165,000,000 authorized Common Shares to the 100,000,000 already authorized Common Shares, for a consolidated total of 265,000,000 authorized Common Shares, as more fully described in the Proxy Statement and as revised by this Supplement, by the statutory votes required pursuant to Section 242(b) of the Delaware General Corporation Law as described in the Proxy Statement. We refer to Proposal 1 as the "Share Consolidation Amendment—Statutory Vote."



2.

To ratify and approve the Share Consolidation Amendment, and the TDS Board's decision to approve such amendment, based on a non-waivable condition voluntarily established by the TDS Board, by (i) approval by a majority of the outstanding Common Shares (excluding Common Shares held by Affiliated Persons), voting separately as a class, and (ii) approval by a majority of the outstanding Special Common Shares (excluding Special Common Shares held by Affiliated Persons), voting separately as a class. We refer to Proposal 2 as the "Share Consolidation Amendment—Ratification Vote."



3.

To consider and approve an amendment, which we refer to as the "Vote Amendment," to the TDS Charter to fix the total percentage voting power of the Series A Common Shares, on the one hand, and Common Shares, on the other hand, in matters other than the election of directors at the aggregate percentage of the voting power of the Series A Common Shares and Common Shares, respectively, immediately prior to the effective time of the foregoing reclassification, subject to adjustment due to changes in the number of outstanding Series A Common Shares, as more fully described in the Proxy Statement and as revised by this Supplement, by the statutory votes required pursuant to Section 242(b) of the Delaware General Corporation Law as described in the Proxy Statement. We refer to Proposal 3 as the "Vote Amendment—Statutory Vote."



4.

To ratify and approve the Vote Amendment, and the TDS Board's decision to approve such amendment, based on a non-waivable condition voluntarily established by the TDS Board, by (i) approval by a majority of the outstanding Common Shares (excluding Common Shares held by Affiliated Persons), voting separately as a class, and (ii) approval by a majority of the outstanding Special Common Shares (excluding Special Common Shares held by Affiliated Persons), voting separately as a class. We refer to Proposal 4 as the "Vote Amendment—Ratification Vote."



5.

To consider and approve a proposal to amend and restate the TDS Charter, which we refer to as the "Ancillary Amendment," to eliminate obsolete and inoperative provisions relating to series of Preferred Shares that are no longer outstanding and relating to Tracking Stock, which has never been issued and which the TDS Board no longer has any intention of issuing, as more fully described in the Proxy Statement, by the statutory votes required pursuant to Section 242(b) of the Delaware General Corporation Law as described in the Proxy Statement.



6.

To consider and approve the adoption of the Telephone and Data Systems, Inc. 2011 Long-Term Incentive Plan, which we refer to as the "Incentive Plan Adoption," related to the Share Consolidation Amendment, as more fully described in the Proxy Statement and as revised by this Supplement, by the vote described in the Proxy Statement.

v

Table of Contents

7.

To consider and approve the adoption of an amendment and restatement of the Telephone and Data Systems, Inc. Compensation Plan for Non-Employee Directors, which we refer to as the "Director Plan Amendment," related to the Share Consolidation Amendment, as more fully described in the Proxy Statement, by the vote described in the Proxy Statement.



8.

To approve a proposal to adjourn the Adjourned Special Meeting, if needed, to solicit additional votes in favor of Proposals 1, 2, 3 and 4, as described in this Supplement, by the vote described in the Proxy Statement. We refer to Proposal 8 as the "Adjournment Proposal."



9.

To transact such other business as may properly be brought before the Adjourned Special Meeting or any and all adjournments thereof by or at the direction of the TDS Board.

        The TDS Board has directed that the foregoing Proposals 1-8, as revised in the manner described in this Supplement, be brought before the Adjourned Special Meeting for approval by the shareholders of TDS.

vi

Table of Contents

TABLE OF CONTENTS

Table of Contents

QUESTIONS AND ANSWERS

        The following describes changes to the information included in the Proxy Statement as a result of the change to the reclassification ratio in the Share Consolidation Amendment and the adjournment of the Special Meeting. This information revises and supplements the Proxy Statement and should be read with the more detailed information contained in the Proxy Statement and in the Supplement below. You may obtain the information incorporated by reference in the Proxy Statement as supplemented hereby without charge by following the instructions under "Where You Can Find More Information" below.

Why am I receiving this Supplement?

        The TDS Board has approved changes to the proposals included in the Proxy Statement. These changes are described more fully below in this Supplement.

        In particular, the TDS Board has approved a change to the Share Consolidation Amendment in Proposals 1 and 2. As revised, each Special Common Share would be reclassified as one Common Share, each Common Share would be reclassified as 1.087 Common Shares and each Series A Common Share would be reclassified as 1.087 Series A Common Shares. The primary purpose of this change is to recognize the fact that the Common Shares have generally traded at a premium to the Special Common Shares. Based on a review of the historical average premium, the TDS Board determined that the holders of Common Shares should receive 8.7% additional shares as compared to the holders of Special Common Shares in the Share Consolidation. In addition, because the Series A Common Shares are convertible into Common Shares on a one-for-one basis, the TDS Board determined that the holders of Series A Common Shares should receive 8.7% additional shares as compared to the holders of Special Common Shares in the Share Consolidation. See "Revised Share Consolidation Amendment" below.

        In addition, certain clarifying changes (not substantive in nature) are being made to the Vote Amendment as originally described in the Proxy Statement. See "Revised Vote Amendment" below.

        In addition, the changes to the Share Consolidation Amendment and the adjournments of the Special Meeting discussed above have an effect on Proposal 6, which we refer to as the "Incentive Plan Adoption," relating to the adoption of the Telephone and Data Systems, Inc. 2011 Long-Term Incentive Plan, which we refer to as the "2011 Incentive Plan." Accordingly, certain changes have been made to Proposal 6 that was included in the Proxy Statement and to the 2011 Incentive Plan, which was attached as Exhibit C to the Proxy Statement.

        See "Changes to Proposal 6—Adoption of Telephone and Data Systems, Inc. 2011 Long-Term Incentive Plan" below.

        In addition, TDS has revised Proposal 8, the Adjournment Proposal, so that it applies to the Adjourned Special Meeting, as defined below. See "Changes to Proposal 8—Adjournment Proposal" below.

What does the TDS Board recommend?

        The TDS Board, including the independent directors, has unanimously approved each proposal, including the revised Share Consolidation Amendment, the revised Vote Amendment, the revised Incentive Plan Adoption and the revised Adjournment Proposal, believes that the adoption of each proposal is in the best interests of TDS and its shareholders and unanimously recommends that you vote "FOR" each of the proposals, as revised by this Supplement.

What is the date, time and place of the Adjourned Special Meeting?

        The adjourned Special Meeting to vote on the revised proposals described in this Supplement, which we refer to as the "Adjourned Special Meeting," will be held on Friday, January 13, 2012, at 11:00 a.m. Chicago time at the Standard Club, 320 S. Plymouth Court, Chicago, Illinois.

2

Table of Contents

What is the new record date for the Adjourned Special Meeting?

        The record date for shareholders to vote at the Adjourned Special Meeting on January 13, 2012 has been changed from the close of business on August 18, 2011 to the close of business on December 9, 2011.

What do I need to do now?

        As a result of the changes to the proposals and the record date, all proxies and broker votes previously submitted will be deemed null and void. YOU MUST SIGN AND RETURN A NEW PROXY CARD OR ATTEND THE ADJOURNED SPECIAL MEETING AND VOTE IN PERSON FOR YOUR VOTE TO BE COUNTED AT THE ADJOURNED SPECIAL MEETING ON JANUARY 13, 2012.

        If you do not expect to be present and vote in person at the Adjourned Special Meeting, please sign and mail the enclosed proxy in the enclosed self-addressed envelope to Computershare Trust Company, N.A., P.O. Box 43126, Providence, Rhode Island 02940-5138, or vote by proxy on the Internet or by phone in accordance with the instructions on the proxy card.

        Proxies given pursuant to this solicitation may be revoked at any time prior to the closing of polls at the Adjourned Special Meeting (by written notice to the Secretary of TDS, by submitting a later dated proxy or by attendance and voting in person at the Adjourned Special Meeting). Once the polls are closed, however, proxies may not be retroactively revoked.

What happens to the vote I previously submitted via proxy or broker instruction?

        All proxies and broker votes previously submitted with respect to the proposals in the Proxy Statement will be deemed null and void. A new proxy card is enclosed to enable you to vote on the proposals listed above at the Adjourned Special Meeting. YOUR VOTE IS IMPORTANT. Whether or not you are able to attend the Adjourned Special Meeting in person, it is important that your shares be represented. If you received a copy of the proxy card by mail, you may sign, date and mail the proxy card in the envelope provided. Your vote can be changed if you attend the Adjourned Special Meeting, withdraw your proxy, and vote in person. Please vote as soon as possible.

What are the changes to the Share Consolidation Amendment in Proposals 1 and 2?

        The Share Consolidation Amendment originally contemplated that each issued Special Common Share would be reclassified as one Common Share. The Share Consolidation Amendment did not originally contemplate reclassification of Common Shares or Series A Common Shares as a greater number of such shares.

        As revised, each Special Common Share would be reclassified as one Common Share, each Common Share would be reclassified as 1.087 Common Shares and each Series A Common Share would be reclassified as 1.087 Series A Common Shares. The purpose of this change is to recognize the fact that the Common Shares have generally traded at a premium to the Special Common Shares. Based on a review of the historical average premium, the TDS Board determined that the holders of Common Shares should receive 8.7% additional shares as compared to the holders of Special Common Shares in the Share Consolidation. Also, because the Series A Common Shares are convertible into Common Shares on a one-for-one basis, the TDS Board determined that the holders of Series A Common Shares should receive 8.7% additional shares as compared to the holders of Special Common Shares in the Share Consolidation. See "Revised Share Consolidation Amendment" below.

3

Table of Contents

        The following shows certain information about the status quo, the original Share Consolidation proposal and the revised Share Consolidation proposal based on shares outstanding as of September 30, 2011 and assuming the Charter Amendments became effective on such date:

1.     Reclassification Ratio

2.     Common Stock Outstanding (in millions)

3.     Percentage of Outstanding Common Stock

4.     Percentage Voting Power in Matters Other than Election of Directors

4

Table of Contents

5.     Percentage Outstanding Shares held by TDS Voting Trust

6.     Percentage Voting Power of TDS Voting Trust in Matters Other than Election of Directors

7.     Total Annual Dividends Paid based on Current Dividend Rate (in millions)

        For additional information regarding TDS' current and proposed equity capitalization, see "Summary Comparison of Current Equity Capitalization with Proposed Capitalization, as Revised" below.

What are the changes to the Vote Amendment in Proposals 3 and 4?

        No substantive changes are being made to the Vote Amendment as originally described in the Proxy Statement. Only certain clarifying changes are being made as discussed below. See "Revised Vote Amendment" below.

What are the changes to the Incentive Plan Adoption proposal in Proposal 6?

        The changes to the Share Consolidation Amendment and the adjournments of the Special Meeting discussed above have an effect on Proposal 6 relating to the adoption of the 2011 Incentive Plan. Accordingly, certain changes have been made to Proposal 6 that was included in the Proxy Statement and to the 2011 Incentive Plan, which was attached as Exhibit C to the Proxy Statement. Proposal 6 and the 2011 Incentive Plan have been revised to provide that if the 2011 Incentive Plan is approved by

5

Table of Contents

shareholders, the 2011 Incentive Plan will be effective as of the effective date of the Charter Amendments, as revised in the manner described in this Supplement (and will be void and of no effect if the revised Charter Amendments are not effectuated). The revised 2011 Incentive Plan also provides that its terms will govern annual bonus deferrals and related employer match awards for calendar years commencing on or after January 1, 2013, and that such deferrals and match awards for calendar years commencing prior to January 1, 2013 will be governed by the Telephone and Data Systems, Inc. 2004 Long-Term Incentive Plan.

        See "Changes to Proposal 6—Adoption of Telephone and Data Systems, Inc. 2011 Long-Term Incentive Plan" below.

What are the changes to the Adjournment Proposal in Proposal 8?

        Proposal 8 in the Proxy Statement was intended to permit TDS to adjourn the Special Meeting on October 6, 2011, if needed, to solicit additional proxies if there were insufficient votes at the time of the Special Meeting to approve Proposal 1, 2, 3 or 4. TDS has revised Proposal 8 so that it applies to the Adjourned Special Meeting, as defined above. As a result, approval of revised Proposal 8 would authorize TDS to adjourn the Adjourned Special Meeting on January 13, 2012, if needed, to solicit additional proxies if there are insufficient votes at the time of the Adjourned Special Meeting to approve Proposal 1, 2, 3 or 4.

        See "Changes to Proposal 8—Adjournment Proposal" below.

What are the federal income tax consequences of the proposals, as revised?

        No gain or loss is expected to be recognized by any of the holders of Special Common Shares, Common Shares or Series A Common Shares as a result of the Charter Amendments, including the revised Share Consolidation Amendment, except to the extent of cash received in lieu of fractional shares.

        See "Federal Income Tax Consequences" below for a more complete discussion of the federal income tax consequences of the Charter Amendments, including the revised Share Consolidation Amendment. You are strongly urged to consult your tax advisor as to the specific tax consequences to you of the Charter Amendments, including the application of federal, state, local and foreign income and other tax laws based on your particular facts and circumstances.

What will happen if the Charter Amendments become effective?

        The following describes the anticipated effects on holders of Special Common Shares, Common Shares and Series A Common Shares if the Charter Amendments, as revised, become effective.

        The following illustration assumes that you own 100 Special Common Shares.

•

Shares: In the Share Consolidation, your 100 Special Common Shares would be reclassified as 100 Common Shares.



•

Votes for Directors: The 100 Common Shares would continue to have 100 votes in the election of 25% of the directors plus one additional director (or a total of four directors based on the current TDS Board size of twelve directors). As of September 30, 2011, holders of Special Common Shares have approximately 48.4% of the aggregate voting power in the election of these four directors. After the Share Consolidation, in the aggregate, the current holders of Special Common Shares would have approximately 46.3% of the voting power in the election of these four directors.



•

Votes for Other Matters: Although the Special Common Shares currently do not have a vote in matters other than the election of directors, the 100 Common Shares into which such Special Common Shares are reclassified would, as Common Shares, vote in the election of directors and on all other matters. In matters other than the election of directors, the voting power of the 100 new Common Shares would float along with the voting power of all other Common Shares so that the total voting power of all Common Shares after the Charter Amendments are effective would equal approximately 43.3% (based on shares outstanding on September 30, 2011) of the total

6

Table of Contents

voting power of all outstanding shares of common stock in matters other than the election of directors (subject to adjustment based on changes in the outstanding Series A Common Shares as discussed below and in the Proxy Statement). As a result of the reclassification of all outstanding Special Common Shares as Common Shares in the Share Consolidation, the initial per share voting power of each Common Share in matters other than the election of directors would be approximately 0.54 votes per share. Accordingly, such 100 Special Common Shares, which currently do not vote in matters other than the election of directors, would initially have approximately 54 votes in matters other than the election of directors after those shares are reclassified as 100 Common Shares in the Share Consolidation, and thereafter would have voting power that would float depending on the number of outstanding Common Shares and Series A Common Shares, as discussed below and in the Proxy Statement.

•

Dividends: Subject to declaration or change in the per share dividend rate by the TDS Board, you would continue to receive a quarterly cash dividend of $0.1175 per share with respect to the 100 Common Shares that you receive upon the reclassification of your 100 Special Common Shares, which is the amount of the per share quarterly dividend all holders of common stock currently receive. The amount of the aggregate quarterly dividend that a holder of 100 Special Common Shares currently receives is $11.75, based on the current quarterly dividend rate of $0.1175 per share. The amount of the aggregate quarterly dividend you would receive as a holder of 100 Common Shares would continue to be $11.75, based on the current quarterly dividend rate of $0.1175 per share.



•

NYSE: The Common Shares would be traded on the NYSE under the symbol "TDS." The Special Common Shares would no longer be outstanding and would cease to trade on the NYSE.

        The following illustration assumes that you own 100 Common Shares.

•

Shares: In the Share Consolidation, your 100 Common Shares would be reclassified as 108 Common Shares and you would receive cash in lieu of 0.7 of a Common Share.



•

Votes for Directors: Currently, the 100 Common Shares have 100 votes in the election of 25% of the directors plus one additional director (or a total of four directors based on the current TDS Board size of twelve directors). After the Share Consolidation, the 108 Common Shares would have 108 votes in the election of these four directors. Currently, holders of Common Shares have approximately 51.6% of the aggregate voting power in the election of these four directors. After the Share Consolidation, the current holders of Common Shares would have approximately 53.7% of the aggregate voting power in the election of these four directors.



•

Votes for Other Matters: The 108 Common Shares would continue to vote in matters other than the election of directors. However, the Common Shares would no longer have one vote per share in such matters. Instead, the voting power of the Common Shares would float so that the total voting power of all Common Shares after the Charter Amendments are effective would equal approximately 43.3% (based on shares outstanding on September 30, 2011) of the total voting power of all outstanding shares of common stock in matters other than the election of directors (subject to adjustment based on changes in the outstanding Series A Common Shares as discussed below and in the Proxy Statement). As a result of the reclassification of all outstanding Special Common Shares as Common Shares in the Share Consolidation, the initial per share voting power of each Common Share would be approximately 0.54 votes per share. Accordingly, the total voting power of such 108 Common Shares would initially decline from 108 votes to approximately 58 votes in matters other than the election of directors after the Charter Amendments are effective and thereafter would have voting power that would float depending on the number of outstanding Common Shares and Series A Common Shares, as discussed below and in the Proxy Statement.



•

Dividends: Subject to declaration or change in the per share dividend rate by the TDS Board, you would continue to receive a quarterly cash dividend of $0.1175 per share with respect to the 108 Common Shares that you receive upon the reclassification of your 100 Common Shares, which is the amount of the per share quarterly dividend all holders of common stock currently receive. The

7

Table of Contents

amount of the aggregate quarterly dividend a holder of 100 Common Shares currently receives is $11.75, based on the current quarterly dividend rate of $0.1175 per share. The amount of the aggregate quarterly dividend you would receive as a holder of 108 Common Shares would increase to $12.69, based on the current quarterly dividend rate of $0.1175 per share.

•

NYSE: The Common Shares would continue to be traded on the NYSE under the symbol "TDS."

        The following illustration assumes that you own 100 Series A Common Shares.

•

Shares: In the Share Consolidation, your 100 Series A Common Shares would be reclassified as 108 Series A Common Shares and you would receive cash in lieu of 0.7 of a Series A Common Share.



•

Votes for Directors: The 108 Series A Common Shares would have 1,080 votes in the election of 75% of the directors less one director (or a total of eight directors based on the current TDS Board size of twelve directors). Because the Series A Common Shares currently have almost 100% of the voting power in the election of these eight directors, the increased number of shares would have no practical effect in the election of these directors.



•

Votes for Other Matters: The 108 Series A Common Shares would also have 1,080 votes in matters other than the election of directors. However, the voting power of the Series A Common Shares in matters other than the election of directors would be fixed based on shares outstanding immediately prior to the effectiveness of the Charter Amendments (approximately 56.7% based on shares outstanding on September 30, 2011) and thereafter could decrease depending on the number of outstanding Common Shares and Series A Common Shares, as discussed below and in the Proxy Statement. The additional Series A Common Shares issued in the Share Consolidation would not increase the aggregate percentage voting power of the Series A Common Shares in matters other than the election of directors above 56.7% (based on shares outstanding on September 30, 2011).



•

Dividends: Subject to declaration or change in the per share dividend rate by the TDS Board, you would continue to receive a quarterly cash dividend of $0.1175 per share with respect to the 108 Series A Common Shares that you receive upon the reclassification of your 100 Series A Common Shares, which is the amount of the per share quarterly dividend all holders of common stock currently receive. The amount of the aggregate quarterly dividend a holder of 100 Series A Common Shares currently receives is $11.75, based on the current quarterly dividend rate of $0.1175 per share. The amount of the aggregate quarterly dividend you would receive as a holder of 108 Series A Common Shares would increase to $12.69, based on the current quarterly dividend rate of $0.1175 per share.



•

NYSE: There is no public market for the Series A Common Shares. The 108 Series A Common Shares would no longer be convertible into Special Common Shares, but would continue to be convertible into Common Shares on a share-for-share basis, or into 108 Common Shares. Thus, the Series A Common Shares would continue to be convertible into a class of stock that is listed and traded on the NYSE.

        See "Revised Share Consolidation Amendment" and "Revised Vote Amendment" below.

What will happen to TDS' outstanding stock-based awards as a result of the revised Share Consolidation Amendment?

        If the revised Share Consolidation Amendment becomes effective, TDS will appropriately adjust outstanding options, restricted stock units and other stock awards issued under the Telephone and Data Systems, Inc. 2004 Long-Term Incentive Plan to reflect the reclassification, and such awards will be settled solely in Common Shares. Such adjustment, including any adjustment to the exercise price of an option or number of Common Shares subject to the award, shall be determined in a manner consistent with requirements of applicable federal tax regulations and other applicable requirements.

8

Table of Contents

Did TDS receive a revised fairness opinion from a financial advisor?

        In deciding to revise the Share Consolidation Amendment, the TDS Board received and considered a revised opinion from Citi to the effect that, as of the date of the opinion, and based upon and subject to the considerations and limitations set forth therein, Citi's work described below under "Other Information Regarding Revised Charter Amendments—Opinion of Financial Advisor" and other factors Citi deemed relevant, the reclassification ratio of one new Common Share for each outstanding Special Common Share and 1.087 new Common Shares for each outstanding Common Share was fair, from a financial point of view, to both the holders of Common Shares and the holders of Special Common Shares (solely in their capacity as holders of Common Shares or holders of Special Common Shares, as the case may be, and disregarding any interest any holder of Common Shares or Special Common Shares, as the case may be, may have in any other equity securities of TDS). The full text of the revised written opinion of Citi, which sets forth the assumptions made, procedures followed, matters considered and limitations on the review undertaken in connection with the opinion, is included in this Supplement as Exhibit B. We urge you to read the revised opinion in its entirety.

        Citi's advisory services and opinion were provided for the information and assistance of the TDS Board in connection with its consideration of the revised Share Consolidation Amendment. Neither Citi's opinion nor the related analyses constituted a recommendation of the proposed Share Consolidation or the proposed reclassification ratio to the TDS Board. Citi's opinion was not intended to be and does not constitute a recommendation, and Citi does not make any recommendation, as to how any holder of TDS shares should vote with respect to the revised Share Consolidation Amendment or any of the other proposals.

        See "Other Information Regarding Revised Charter Amendments—Opinion of Financial Advisor" below.

Did the independent directors of TDS receive financial and legal advice in connection with the changes to the revised Share Consolidation Amendment?

        In connection with their consideration of the changes to the Share Consolidation Amendment, the independent directors received the advice of Credit Suisse as financial advisor, and Bass, Berry & Sims as legal advisor, to the independent directors.

How does the TDS Voting Trust intend to vote with respect to the revised proposals?

        The TDS Voting Trust has advised TDS that it intends to vote FOR the revised proposals.

        However, approval of the revised Share Consolidation Amendment in Proposals 1 and 2 and the revised Vote Amendment in Proposals 3 and 4 is not assured even if the TDS Voting Trust votes in favor of such proposals, due to the class votes described in the Proxy Statement.

What is the number of outstanding shares and voting power in matters other than the election of directors based on shares outstanding on September 30, 2011?

        Each holder of outstanding Common Shares or Preferred Shares is entitled to one vote for each Common Share or Preferred Share held in such holder's name. Each holder of Series A Common Shares is entitled to ten votes for each Series A Common Share held in such holder's name. The following shows information relating to the outstanding shares, votes per share and total voting power

9

Table of Contents

(for all such shares in total and for each of the Series A Common Shares and Common Shares as a class) of such shares as of September 30, 2011:

        The above also shows the individual class voting power of the Series A Common Shares and of the Common Shares based on shares outstanding as of September 30, 2011.

        Also, under the TDS Charter, the holders of Special Common Shares do not vote for matters other than the election of certain directors except as required by law or regulation. However, the holders of Special Common Shares have a statutory class vote under the Delaware General Corporation Law with respect to the Share Consolidation Amendment. In addition, the TDS Board has determined to voluntarily submit the Share Consolidation Amendment and the Vote Amendment for approval and ratification by a majority vote of the holders of Special Common Shares other than Affiliated Persons (voting separately as a class), as well as by a majority vote of the holders of Common Shares other than Affiliated Persons (voting separately as a class). Accordingly, the following shows information relating to the outstanding shares, votes per share and total voting power of the Special Common Shares as of September 30, 2011:

What is the number of shares held by Affiliated Persons as of September 30, 2011?

        In the ratification votes under Proposals 2 and 4, shares held by Affiliated Persons will be excluded. The following shows the number of outstanding Common Shares and Special Common Shares as of September 30, 2011 that are considered to be held by Affiliated Persons for purposes of these votes:

What votes are required for approval of the revised proposals?

        The votes required for approval of the revised proposals are the same as were described in the Proxy Statement, except that, in addition to the votes described in the Proxy Statement, Proposal 1 will also require the approval of the holders of a majority of the voting power of the Series A Common Shares outstanding and entitled to vote thereon, voting as a separate class.

        The vote of the holders of Series A Common Shares, Common Shares and Preferred Shares in Proposal 1 will also serve to satisfy the vote required for the issuance of additional Common Shares and Series A Common Shares upon the reclassification pursuant to Section 312.03 of the NYSE Listed Company Manual.

What is the procedure for effecting the Charter Amendments and the impact on holders of stock certificates?

        If shareholders approve the proposed Charter Amendments, including the revised Share Consolidation Amendment, and the TDS Board determines to implement the proposed Charter

10

Table of Contents

Amendments, TDS will file a Restated Certificate of Incorporation with the Secretary of State of the State of Delaware. The Charter Amendments would become effective at the time and date specified in such Restated Certificate of Incorporation, which we refer to as the "Effective Time."

        Beginning at the Effective Time, without further action by the holders of TDS shares, (i) existing certificates representing Special Common Shares will automatically represent an equal number of Common Shares, (ii) existing certificates representing Common Shares will automatically represent an equal number of Common Shares, and (iii) existing certificates representing Series A Common Shares will automatically represent an equal number of Series A Common Shares. To the extent feasible, certificates will not be distributed with respect to the 0.087 additional shares. Such additional shares will be distributed to record holders in book entry form, to the extent feasible. Following the Effective Time, each holder of Common Shares and Series A Common Shares will receive a statement showing the number of additional shares credited to such holder and a check in payment for any fractional shares.

Should I send in my stock certificates?

        No. You should not send in your existing stock certificates representing shares of TDS. It will not be necessary for holders of Special Common Shares, Common Shares or Series A Common Shares to exchange their existing certificates for new certificates.

        Shareholders should retain all certificates which currently represent Special Common Shares because such certificates will continue to represent Special Common Shares if the Share Consolidation Amendment does not become effective, and will represent Common Shares if the Share Consolidation Amendment becomes effective.

        Shareholders should also retain all certificates representing Common Shares and Series A Common Shares. Such certificates will continue to represent the number of Common Shares or Series A Common Shares, respectively, identified on the certificates, whether or not the Share Consolidation Amendment becomes effective. If the Share Consolidation Amendment becomes effective, Computershare will distribute the additional Common Shares resulting from the Share Consolidation Amendment with respect to outstanding Common Shares and the additional Series A Common Shares resulting from the Share Consolidation Amendment with respect to outstanding Series A Common Shares, and cash in lieu of fractional shares, in the following manner. Holders of Common Shares and Series A Common Shares will not be required to surrender certificates to receive the additional shares or cash in lieu of fractional shares.

        Except as discussed in the answer to the next question, no fractional shares will be issued in connection with the reclassification of each Common Share as 1.087 Common Shares or the reclassification of each Series A Common Share as 1.087 Series A Common Shares. The number of additional Common Shares or Series A Common Shares to which each holder of Common Shares or Series A Common Share is entitled as a result of the Share Consolidation will be determined as follows. The number of Common Shares or Series A Common Shares held of record by each record holder at the Effective Time will be multiplied by 0.087. If the product so obtained is not a whole number, the result will be rounded down to the next smaller whole number and holders of Common Shares or Series A Common Shares will be issued such whole number of Common Shares or Series A Common Shares, respectively. To the extent feasible, certificates will not be distributed with respect to the 0.087 additional shares. Such additional shares will be distributed to record holders in book entry form, to the extent feasible. In lieu of any fractional Common Share or fractional Series A Common Share to which such record holder would have been entitled but for the foregoing rounding, TDS will pay to such record holder an amount in cash equal to the product obtained by multiplying such fraction by the closing price of a Common Share on the NYSE on the last full trading day before the Effective Time.

        If the Share Consolidation Amendment becomes effective, the former holders of Special Common Shares will be able to request Common Share certificates in exchange for the old Special Common Share certificates, but there will be no need to do so. In addition, holders of Common Shares and Series A Common Shares who receive additional shares in book entry form may request certificates for such shares, but there will be no need to do so. You can make such requests by contacting TDS'

11

Table of Contents

transfer agent and registrar, Computershare Trust Company, N.A., which we refer to as "Computershare," at 1-877-337-1575 or online at www.computershare.com.

        If you are the beneficial owner of shares held in "street name" by a broker, bank, or other nominee, you should contact such nominee to determine how you will receive your shares and cash in lieu of any fractional shares.

What will happen if I participate in one of the TDS Dividend Reinvestment Plans?

        TDS sponsors a Special Common Share Automatic Dividend Reinvestment and Stock Purchase Plan, which we refer to as the "Special Common Share DRIP," a Common Share Automatic Dividend Reinvestment and Stock Purchase Plan, which we refer to as the "Common Share DRIP," and a Series A Common Share Automatic Dividend Reinvestment Plan, which we refer to as the "Series A DRIP."

        Participants in the Special Common Share DRIP will automatically have all of the Common Shares into which such participant's Special Common Shares in the Special Common Share DRIP have been reclassified credited to the Common Share DRIP in book entry form. Whole and fractional shares will be credited to the accounts of participants. Shareholders can request certificates to be issued as set forth in the Common Share DRIP. The Special Common Share DRIP will be terminated if the Share Consolidation Amendment becomes effective because there will no longer be any Special Common Shares authorized or outstanding.

        Participants in the Common Share DRIP will automatically have the additional Common Shares received in the reclassification credited to the account of such participant in the Common Share DRIP in book entry form. Pursuant to the Common Share DRIP, whole and fractional shares will be credited to the accounts of participants. As a result, participants will be issued fractional shares in lieu of a cash payment. Shareholders can request certificates to be issued as set forth in the Common Share DRIP.

        Participants in the Series A DRIP will automatically have the additional Series A Common Shares received in the reclassification credited to the account of such participant in the Series A DRIP in book entry form. Pursuant to the Series A DRIP, whole and fractional shares will be credited to the accounts of participants. As a result, participants will be issued fractional shares in lieu of a cash payment. Shareholders can request certificates to be issued as set forth in the Series A DRIP.

Do shareholders have dissenters' rights with respect to the revised Share Consolidation Amendment?

        No holders of capital stock of TDS have the right to dissent and receive payment for their shares (sometimes referred to as appraisal rights) under Delaware law in connection with the revised Share Consolidation Amendment or with respect to any of the other proposals.

Do shareholders have additional possible regulatory requirements as a result of the revised Share Consolidation Amendment?

        Shareholders meeting applicable size thresholds who will hold TDS common stock valued at $66 million or more after the Share Consolidation may have a pre-merger notification filing obligation under the Hart-Scott-Rodino Antitrust Improvements Act of 1976, as amended, unless the shareholder qualifies for an exemption to the filing requirements under such Act.

Can the Adjourned Special Meeting to be held on January 13, 2012 be further adjourned or postponed?

        Even if a quorum is present, holders of a majority of the voting power of the voting stock of TDS represented in person or by proxy may adjourn or postpone the Adjourned Special Meeting. Because it holds a majority of the voting power of all classes of stock of TDS, the TDS Voting Trust has the voting power to propose and approve an adjournment or postponement.

12

Table of Contents

        In addition, the TDS Board is asking shareholders to approve Proposal 8, as revised, which would give the persons named in the enclosed proxy discretionary authority to further adjourn the Adjourned Special Meeting to solicit additional votes for Proposal 1, 2, 3 or 4.

        Also, the Adjourned Special Meeting could be postponed before it is convened, and any adjournment or postponement can be postponed before it is convened. TDS does not currently have any expectation that the Adjourned Special Meeting would be adjourned or postponed.

Who is soliciting proxies for the Adjourned Special Meeting?

        Your proxy is solicited by the TDS Board and the cost of solicitation will be paid by TDS. Officers, directors and regular employees of TDS, acting on its behalf, may also solicit proxies by mail, email, advertisement, telephone, telecopy, press release, employee communication, postings on TDS' Internet website and Intranet website or in person. No remuneration, other than regular compensation, will be paid to any such officer, director or employee in connection with such activities. TDS has not engaged any agents to solicit proxies and no commission or other remuneration is being paid or given directly or indirectly for soliciting such proxies.

What do I do if I have additional questions about voting procedures or need additional copies of this Supplement, the Proxy Statement or the Proxy Cards?

        If you have any questions about voting procedures prior to the Adjourned Special Meeting, please contact TDS' information agent, MacKenzie Partners, Inc., at the address, telephone number, fax number or email address indicated below. Any substantive questions about the proposals will be directed to TDS. The services of MacKenzie Partners are ministerial and will not involve any recommendation by MacKenzie Partners with respect to the proposals or encouragement to vote in a particular manner.

        Additional copies of this Supplement, the Proxy Statement or the proxy cards may be obtained from the information agent as follows:

105 Madison Avenue
New York, New York 10016
(212) 929-5500 (Call Collect)

or

CALL TOLL-FREE (800) 322-2885
FAX: (212) 929-0308
TDSproxy@mackenziepartners.com

13

Table of Contents

SUMMARY COMPARISON OF CURRENT EQUITY CAPITALIZATION
WITH PROPOSED CAPITALIZATION, AS REVISED

        The following is an updated summary of the differences between the equity capitalization of TDS as of September 30, 2011, under the column captioned "Status Quo," and the equity capitalization of TDS on a pro forma basis as of September 30, 2011, under the column captioned "Pro-Forma," as if the revised Charter Amendments had become effective on that day, reflecting the reclassification ratio of one Common Share per Special Common Share, 1.087 Common Shares per Common Share and 1.087 Series A Common Shares per Series A Common Share. Reference to shares held by "Non-Voting Trust Affiliated Persons" is comprised of shares held by members of the Carlson family outside of the TDS Voting Trust and shares held by directors and executive officers of TDS outside of the TDS Voting Trust. "Other Shareholders" refers to holders of Series A Common Shares, Common Shares or Special Common Shares other than the Affiliated Persons. The following numbers are rounded and assume that fractional shares will be issued rather than redeemed for cash. (Some columns may not total due to rounding.)

        NOTE: Shares that are Special Common Shares in the Status Quo column represent Common Shares in the Pro Forma column following the Share Consolidation.

1.     Authorized Shares

14

Table of Contents

2.     Outstanding Shares

3.     Outstanding Shares as a Percent of Common Equity

15

Table of Contents

4.     Votes for Directors

5.     Voting Power in Election of Directors

16

Table of Contents

6.     Percentage Voting Power in Election of Directors

7.     Votes per Share in Matters Other than Election of Directors

17

Table of Contents

8.     Voting Power in Matters Other than Election of Directors (using Pro-Forma voting power per Common Share of approximately 0.53668 assuming Share Consolidation had occurred on September 30, 2011) (2)

9.     Percentage Voting Power in Matters Other than Election of Directors

18

Table of Contents

10.  Treasury Shares and Shares held by Subsidiary

11.  Shares Reserved for Issuance

19

Table of Contents

12.  Authorized Shares Available for Issuance based on Shares and Reserves as of September 30, 2011 (Authorized Shares (Item 1) less Outstanding Shares (Item 2) less Treasury Shares and Shares held by Subsidiary (Item 10) and less Shares Reserved for Issuance (Item 11))

13.  Additional Shares to be Reserved for Issuance (per Proposal 6)

14.  Authorized Shares Available for Issuance After Deductions of Additional Shares to be Reserved for Issuance (Authorized Shares Available for Issuance based on Shares and Reserves as of September 30, 2011 (Item 12) less Additional Shares to be Reserved for Issuance (Item 13))

20

Table of Contents

15.  Cash Dividends

16.  Conversion Rights