As previously announced, on February 1, 2017, Old Line Bancshares, Inc., a Maryland corporation (“Old Line”), entered into an Agreement and Plan of Merger with DCB Bancshares, Inc., a Maryland corporation (“DCBB”) and the parent company of Damascus Community Bank (“DCB”), to which DCBB will be merged with and into Old Line (the “Merger”). As previously disclosed, consummation of the Merger is subject to certain closing conditions, including the receipt of required regulatory approvals. Such approvals include approval of the Board of Governors of the Federal Reserve System (the “FRB”) and the Maryland Office of the Commissioner of Financial Regulation (the “Maryland Commissioner”) of the Merger and of the Federal Deposit Insurance Corporation (the “FDIC”) and the Maryland Commissioner for the merger of DCB into Old Line Bank (the “Bank Merger”). We received FRB approval for the Merger on May 2, 2017, FDIC approval of the Bank Merger as of June 8, 2017, and Maryland Commissioner approval of the Merger and the Bank Merger on June 15, 2017. Accordingly, all required regulatory approvals with respect to the Merger have now been received. Among other remaining conditions to closing, the Merger must be approved by the stockholders of DCBB, and a meeting of DCBB stockholders to vote on the Merger has been scheduled for June 28, 2017.

Important Additional Information.

This communication does not constitute an offer to sell or the solicitation of an offer to buy any securities or a solicitation of any vote or approval. This report contains statements relating to a proposed merger between Old Line and DCBB that is the subject of proxy statement/prospectus included in an amendment to Old Line’s Registration Statement on Form S-4 filed with the Securities and Exchange Commission (the “SEC”) on May 8, 2017.

This report is not a substitute for the proxy statement/prospectus or any other document that Old Line has filed or may file with the SEC or that Old Line or DCBB has sent or may send to its stockholders in connection with the Merger and DCBB’s board of directors’ solicitation of proxies in connection therewith. INVESTORS AND STOCKHOLDERS ARE URGED TO READ THE PROXY STATEMENT/PROSPECTUS AND ALL OTHER RELEVANT DOCUMENTS THAT HAVE BEEN OR MAY BE FILED WITH THE SEC OR SENT TO STOCKHOLDERS, INCLUDING THE FINAL PROXY STATEMENT/PROSPECTUS, AS THEY BECOME AVAILABLE BECAUSE THEY CONTAIN AND WILL CONTAIN IMPORTANT INFORMATION ABOUT THE PROPOSED MERGER. Investors and security holders will be able to obtain the documents (as available) free of charge at the SEC’s website, www.sec.gov. Copies of the documents filed with the SEC by Old Line will be available free of charge on Old Line’s website at www.oldlinebank.com under the tab “Investor Relations” and then under the heading “SEC Filings” or by contacting Mark A. Semanie at (301)430-2500. You may also read and copy any reports, statements and other information filed with the SEC at the SEC’s Public Reference Room at 100F Street, NE, Washington DC. Information about the operation of the SEC Public Reference Room may be obtained by calling the SEC at 1-800-SEC-0330. The information on Old Line’s website is not, and shall not be deemed to be, a part of this report or incorporated into other filings Old Line makes with the SEC.

DCBB and its respective directors, executive officers and members of management may be deemed to be participants in the solicitation of proxies from the stockholders of DCBB in connection with the Merger. Information regarding the interests of these participants and other persons who may be deemed participants in the Merger is set forth in the proxy statement/ prospectus referred to above.

About Old Line Bancshares, Inc. (NASDAQ:OLBK)

Old Line Bancshares, Inc. is the holding company of Old Line Bank (The Bank). The Bank is a chartered trust company engaged in commercial banking business, making various types of loans, investments and accepting deposits. It markets its financial services to small to medium sized businesses, entrepreneurs, professionals, consumers and clients. The Bank, through its division Old Line Financial Services, provides retirement planning and products, as well as investment services. Its lending activities consists of short to medium term commercial business loans, commercial real estate loans, real estate construction loans, home equity loans and consumer installment loans, both secured and unsecured. The Bank monitors its investment portfolio and it usually classifies investments in the portfolio as available for sale. It offers a range of deposit products that include demand, negotiable order of withdrawal (NOW), money market and savings accounts, as well as certificates of deposit.