| Year | Champion | Runner-Up | Series |
|---|---|---|---|
| 2025 | Strasburg Express | Charlottesville Tom Sox | 2-1 |
| 2024 | Charlottesville Tom Sox | Purcellville Cannons | 2-1 |
| 2023 | Harrisonburg Turks | Charlottesville Tom Sox | 2-0 |
| 2022 | Charlottesville Tom Sox | Woodstock River Bandits | 2-0 |
| 2021 | Strasburg Express | Waynesboro Generals | 2-0 |
| 2020 | No Season (COVID-19) | - | N/A |
| 2019 | Charlottesville Tom Sox | Strasburg Express | 2-0 |
| 2018 | New Market Rebels | Charlottesville Tom Sox | 2-0 |
| 2017 | Charlottesville Tom Sox | Strasburg Express | 2-1 |
| 2016 | Strasburg Express | Waynesboro Generals | 2-0 |
| 2015 | Strasburg Express | Staunton Braves | 2-1 |
| 2014 | Waynesboro Generals | Charles Town Cannons | 2-1 |
| 2013 | Waynesboro Generals | Strasburg Express | 2-1 |
| 2012 | Harrisonburg Turks | Winchester Royals | 3-1 |
| 2011 | Covington Lumberjacks | Rockbridge Rapids | 2-1 |
| 2010 | Luray Wranglers | Front Royal Cardinals | 2-0 |
| 2009 | Haymarket Senators | Covington Lumberjacks | 3-1 |
| 2008 | Luray Wranglers | Covington Lumberjacks | 3-0 |
| 2007 | Waynesboro Generals | Luray Wranglers | 4-1 |
| 2006 | Luray Wranglers | Staunton Braves | 3-2 |
| 2005 | Covington Lumberjacks | New Market Rebels | 2-1 |
| 2004 | Winchester Royals | Staunton Braves | 2-0 |
| 2003 | Winchester Royals | New Market Rebels | 3-2 |
| 2002 | New Market Rebels | Covington Lumberjacks | 3-1 |
| 2001 | Winchester Royals | Covington Lumberjacks | 3-2 |
| 2000 | Harrisonburg Turks | Staunton Braves | 3-0 |
| 1999 | Staunton Braves | Winchester Royals | 3-0 |
| 1998 | Waynesboro Generals | Staunton Braves | 3-0 |
| 1997 | Winchester Royals | Front Royal Cardinals | Forfeit |
| 1996 | Staunton Braves | Harrisonburg Turks | 3-1 |
| 1995 | Staunton Braves | Waynesboro Generals | 3-0 |
| 1994 | New Market Rebels | Harrisonburg Turks | 3-2 |
| 1993 | Winchester Royals | Staunton Braves | 3-2 |
| 1992 | Winchester Royals | Harrisonburg Turks | 3-1 |
| 1991 | Harrisonburg Turks | Front Royal Cardinals | 3-1 |
| 1990 | Winchester Royals | Staunton Braves | 3-2 |
| 1989 | New Market Rebels | Harrisonburg Turks | 3-1 |
| 1988 | Waynesboro Generals | Madison Blue Jays | 3-2 |
| 1987 | Winchester Royals | Waynesboro Generals | 3-0 |
| 1986 | Front Royal Cardinals | Harrisonburg Turks | 3-1 |
| 1985 | Staunton Braves | New Market Rebels | 3-0 |
| 1984 | Waynesboro Generals | Harrisonburg Turks | 3-0 |
| 1983 | Winchester Royals | Staunton Braves | 4-3 |
| 1982 | Winchester Royals | New Market Rebels | 3-0 |
| 1981 | Winchester Royals | New Market Rebels | 4-0 |
| 1980 | Winchester Royals | New Market Rebels | 3-1 |
| 1979 | Winchester Royals | Madison Blue Jays | 4-3 |
| 1978 | Madison Blue Jays | Harrisonburg Turks | 4-1 |
| 1977 | Harrisonburg Turks | Waynesboro Generals | 4-0 |
| 1976 | Staunton Braves | Harrisonburg Turks | 4-0 |
| 1975 | Madison Blue Jays | Harrisonburg Turks | 4-2 |
| 1974 | Shenandoah Indians | Waynesboro Generals | 4-2 |
| 1973 | Shenandoah Indians | Madison Blue Jays | 4-2 |
| 1972 | Shenandoah Indians | Charlottesville Hornets | 4-2 |
| 1971 | Harrisonburg Turks | Shenandoah Indians | 4-0 |
| 1970 | Harrisonburg Turks | New Market Rebels | 4-1 |
| 1969 | Harrisonburg Turks | Staunton Braves | 4-0 |
| 1968 | Luray Colonials | Harrisonburg Turks | 4-0 |
| 1967 | Luray Colonials | Harrisonburg Turks | 2-0 |
| 1966 | Luray Colonials | Shenandoah Indians | 4-1 |
| 1965 | Luray Colonials | New Market Rebels | 4-2 |
| 1964 | Harrisonburg Turks | Shenandoah Indians | 4-0 |
| 1963 | Shenandoah Indians | New Market Rebels | 4-1 |
| 1962 | Harrisonburg Turks | Shenandoah Indians | 4-2 |
| 1961 | Shenandoah Indians | Harrisonburg Turks | 4-0 |
| 1960 | Shenandoah Indians | Staunton Braves | 4-3 |
| 1959 | Harrisonburg Turks | New Market Rebels | 4-2 |
| 1958 | Harrisonburg Turks | New Market Rebels | 4-3 |
| 1957 | Staunton Braves | Harrisonburg Turks | 4-3 |
| 1956 | Staunton Braves | Shenandoah Indians | 4-2 |
| 1955 | Harrisonburg Turks | Shenandoah Indians | 4-3 |
| 1954 | Staunton Braves | Elkton Blue Sox | 4-1 |