Winland : 2022 Proxy Statement

WINLAND HOLDINGS CORPORATION

424 North Riverfront Drive, Suite 200

Mankato, Minnesota 56001

July 13, 2022

Dear Shareholder:

You are cordially invited to attend the Annual Meeting of Shareholders (the "Annual Meeting") of Winland Holdings Corporation ("Winland" or the "Company"), which is scheduled for August 24, 2022, at 9:00 a.m. CDT, at Fredrikson & Byron P.A., 200 South Sixth Street, Suite 4000, Minneapolis, Minnesota 55402. At the Annual Meeting, we will submit proposals to (1) elect four (4) directors to continue to serve on our Board of Directors for a term ending on the date of the next Annual Meeting, (2) fix the size of the Board of Directors at five (5) directors, and (3) ratify the appointment of Baker Tilly US, LLP as the Company's independent registered public accounting firm for the fiscal year ending December 31, 2022.

These proposals are more fully described in the accompanying Proxy Statement. Any action may be taken on the foregoing proposals on the date specified above for the Annual Meeting, or on any date or dates to which the Annual Meeting may be adjourned. The Board of Directors is not aware of any other business to come before the Annual Meeting.

The Proxy Statement contains important information; please read it carefully. Please also keep in mind that the information contained in these documents should be treated as confidential and should be used only to evaluate the proposals described herein.

The Board of Directors recommends that you vote "FOR" each director nominee named in the Proxy Statement, "FOR" the proposal to fix the size of the Board of Directors at five (5) directors, and "FOR" ratification of the appointment of Baker Tilly US, LLP as the Company's independent registered public accounting firm for the fiscal year ending December 31, 2022. Your vote is important to us. If you are a record holder, whether or not you plan to attend the

Annual Meeting, please vote your proxy via the internet or telephone or complete, sign and return the enclosed proxy card. If you hold your shares in street name, meaning that your shares are held in the name of a broker, bank, trust or other nominee as custodian, you may vote by completing the voting instruction form provided to you by your broker or nominee.

On behalf of the Board of Directors,

/s/ Matthew D. Houk

Chairman, Chief Executive Officer, Chief

Financial Officer

WINLAND HOLDINGS CORPORATION

424 North Riverfront Drive, Suite 200

Mankato, Minnesota 56001

NOTICE OF ANNUAL MEETING OF SHAREHOLDERS

TO BE HELD AUGUST 24, 2022

The Annual Meeting of Shareholders (the "Annual Meeting") of Winland Holdings Corporation, a Minnesota corporation ("Winland" or the "Company"), will be held on August 24, 2022, at 9:00 a.m. CDT, at Fredrikson & Byron P.A., 200 South Sixth Street, Suite 4000, Minneapolis, Minnesota 55402, for the following purposes:

• To elect four (4) directors for a term ending on the date of the next Annual Meeting.
• To consider and vote upon a proposal to fix the size of the Board of Directors at five
  (5) directors.
• To ratify the appointment of Baker Tilly US, LLP as the Company's independent registered public accounting firm for the fiscal year ending December 31, 2022.
• To transact such other business as may properly come before the Annual Meeting or any postponement or adjournment thereof.

Any action may be taken on the foregoing proposals on the date specified above for the Annual Meeting, or on any date or dates to which the Annual Meeting may be adjourned. The Board of Directors is not aware of any other business to come before the Annual Meeting.

Shareholders of record at the close of business on June 29, 2022 are entitled to notice of, and to vote at, the Annual Meeting. Each shareholder is entitled to one vote for each share of common stock held at that time. A list of these shareholders will be open for examination by any shareholder for any purpose germane to the Annual Meeting for a period of ten days prior to the Annual Meeting at the Company's principal executive office at 424 North Riverfront Drive, Suite 200, Mankato, Minnesota 56001.

You can vote your proxy by internet, telephone or mail by following the instructions set forth below:

Voting by Internet: You can vote at www.investorvote.com/WELX, 24 hours a day, seven days a week. You will need the 15-Digit control number included on your proxy card.

Voting by Telephone: You can vote using touch-tone telephone by calling 1-800-652-8683, 24 hours a day, seven days a week. You will need the 15-digit control number included on your proxy card.

Voting by Mail: You may complete, sign and return by mail the proxy card sent to you together with the printed copies of the proxy materials. The proxy card should be mailed to Proxy Service, c/o Computershare Investor Services, PO Box 505008, Louisville, KY 40233-9814.

Please vote as soon as possible to record your vote promptly, even if you plan to attend the Annual Meeting.

If you are a record holder and attend the Annual Meeting, you may, if you wish, revoke your prior proxy and vote in person on all matters brought before the Annual Meeting. If you hold your shares in street name, meaning that your shares are held in the name of a broker, bank, trust or other nominee as custodian, you may vote by completing the voting instruction form provided to you by your broker or nominee. You may not vote your shares in person at the Annual Meeting unless you obtain a legal proxy from your broker or nominee.

By Order of the Board of Directors,

/s/ Matthew D. Houk

Chairman, Chief Executive Officer, Chief

Financial Officer

Mankato, Minnesota

July 13, 2022

TO ASSURE YOUR REPRESENTATION AT THE ANNUAL MEETING, PLEASE SIGN, DATE AND RETURN THE ENCLOSED PROXY CARD WHETHER OR NOT YOU EXPECT TO ATTEND IN PERSON. SHAREHOLDERS WHO ATTEND THE ANNUAL MEETING MAY REVOKE THEIR PRIOR PROXIES AND VOTE IN PERSON IF THEY SO DESIRE.

WINLAND HOLDINGS CORPORATION

___________________________________

PROXY STATEMENT

for

Annual Meeting of Shareholders To Be Held on August 24, 2022

___________________________________

SUMMARY

This summary highlights selected information from this Proxy Statement and may not contain all of the information that is important to you. To better understand the proposals to be voted on at the Annual Meeting, you should carefully read this entire Proxy Statement.

When and Where is the Annual Meeting?

The Annual Meeting of Shareholders (the "Annual Meeting") of Winland Holdings Corporation ("Winland" or the "Company") will be held on August 24, 2022, at 9:00 a.m. CDT, at Fredrikson & Byron P.A., 200 South Sixth Street, Suite 4000, Minneapolis, Minnesota 55402.

What Will Be Voted on at the Annual Meeting?

Shareholders will vote on the following matters:

Proposal 1 - To elect the four (4) directors named in this Proxy Statement for a term ending on the date of the next Annual Meeting;

Proposal 2 - To fix the size of the Winland Board of Directors at five (5) directors; and

Proposal 3 - To ratify the appointment of Baker Tilly US, LLP as the Company's independent registered public accounting firm for the fiscal year ending December 31, 2022.

In addition, the shareholders will consider such other business as may properly come before the Annual Meeting or any postponement or adjournment thereof.

What is the Board of Directors Recommendation Regarding Voting?

The Board of Directors believes that approval of these proposals is in the best interests of Winland and its shareholders and recommends that shareholders vote "FOR" the election of each director, "FOR" the proposal to fix the size of the Board of Directors at five (5) directors, and "FOR" the ratification of the appointment of Baker Tilly US, LLP as the Company's independent registered public accounting firm for the fiscal year ending December 31, 2022.

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