The Virginia Sheriffs’ Association (VSA) was founded in 1933. A listing of VSA past presidents from 1959 until present are listed below.
- 2023-2024 – Lenny Millholland, Frederick County
- 2022-2023 – Fred S. Clark, Halifax County
- 2021-2022 – Kevin W. Hall, Alleghany County-Covington
- 2020-2021 – Darrell W. Warren, Jr., Gloucester County
- 2019-2020 – Timothy C. Carter, Shenandoah County
- 2018-2019 – Steve F. Dempsey, King George County
- 2017-2018 – Vanessa R. Crawford, City of Petersburg
- 2016-2017 – Gabe A. Morgan, City of Newport News
- 2015-2016 – Richard A. Vaughan, Grayson County
- 2014-2015 – Arthur Townsend, Jr., Lunenburg County
- 2013-2014 – Jack Weisenburger, City of Bristol
- 2012-2013 – Beth Arthur, Arlington County
- 2011-2012 – J. D. Diggs, York County-Poquoson
- 2010-2011 – Ryant L. Washington, Fluvanna County
- 2009-2010 – Charles E. Jett, Stafford County
- 2008-2009 – Steve M. Draper, City of Martinsville
- 2007-2008 – Robert J. McCabe, City of Norfolk
- 2006-2007 – Thomas D. Jones, Charlotte County
- 2005-2006 – Raleigh H. Isaacs, Sr., Suffolk City
- 2004-2005 – James R. Woodley, Brunswick County
- 2003-2004 – G. Harold Plaster, Pittsylvania County
- 2002-2003 – Ronald D. Crockett, Lancaster County
- 2001-2002 – B. J. Roberts, City of Hampton
- 2000-2001 – Lynn C. Armentrout, Warren County
- 1999-2000 – Frank Drew, Virginia Beach City
- 1998-1999 – Robin P. Stanaway, Gloucester County
- 1997-1998 – Terry W. Hawkins, Albemarle County
- 1996-1997 – Robert D. Crockett, Accomack County
- 1995-1996 – F. W. Howard, Jr., New Kent County
- 1994-1995 – James Bowman, Charles City County
- 1993-1994 – James H. Dunning, Alexandria City
- 1992-1993 – Vernie W. Francis, Jr., Southampton County
- 1991-1992 – W. Alvin Hudson, Roanoke City
- 1990-1991 – J. Irving Baines, Suffolk City
- 1989-1990 – Earl D. Sasser, Greensville County
- 1988-1989 – Clarence W. Dobson, King George County
- 1987-1988 – E. Stuart Kitchen, Jr., Sussex County
- 1986-1987 – Clay B. Hester, Newport News City
- 1985-1986 – Robert E. Peters, Culpeper County
- 1984-1985 – Charles W. Jackson, Westmoreland County
- 1983-1984 – Emmett L. Wingo, Chesterfield County
- 1982-1983 – H. T. Harris, Mecklenburg County
- 1981-1982 – Everett B. Obenshain, Jr., Salem City
- 1980-1981 – Marshall E. Honaker, Bristol City
- 1979-1980 – Carl H. Wells, Bedford County
- 1978-1979 – Andrew J. Winston, Richmond City
- 1977-1978 – Charlie A. Hodnett, Campbell County
- 1976-1977 – Paul J. Puckett, Roanoke City
- 1975-1976 – John R. Newhart, Chesapeake City
- 1974-1975 – Ottie J. Moore, Caroline County
- 1973-1974 – Jack Cundiff, Bedford County
- 1972-1973 – Luther Cox, Fauquier County
- 1971-1972 – Elwood Clements, Arlington County
- 1970-1971 – John Atwood, Prince George County
- 1969-1970 – J. Tyler Wolfe, Smyth County
- 1968-1969 – Raymond C. Pace, Charlottesville City
- 1967-1968 – John B. Vaughan, Jr., Hanover County
- 1966-1967 – A. Hill Burton, Dinwiddie County
- 1965-1966 – Kermit E. Allman, Roanoke City
- 1964-1965 – James G. Knight, Jr., Nansemond County
- 1963-1964 – Harry B. Hartman, Jr., Petersburg City
- 1962-1963 – John E. Kent, Augusta County
- 1961-1962 – M. A. Owens, Portsmouth City
- 1960-1961 – William B. Chittum, Rockbridge County
- 1959-1960 – John F. Taylor, Fairfax County