| 2009 |
Roanoke Valley (Bo Painter/Paul Brammer) |
| 2008 |
Roanoke Valley (Bo Painter/Paul Brammer) |
| 2007 |
Roanoke Valley (Bo Painter/Paul Brammer) |
| 2006 |
Northern Neck (Kyle Allwine/Jeremiah Cawthone) |
| 2005 |
Northern Neck (Kenny Allwine/Matt Jaquith) |
| 2004 |
Northern Neck (David Ward/Justin Stutler) |
| 2003 |
Northern Neck (David Ward/Justin Stutler) |
| 2002 |
Northern Neck |
| 2001 |
Northern Neck |
| 2000 |
Northern Neck (David Ward/Justin Stutler) |
| 1999 |
Roanoke Valley (Doug Coffman/Matt Stump) |
| 1998 |
Doric (Adam McLamb/Greg McLamb) |
| 1997 |
Cmdr W. L. Herndon (Josef Garcia/Sean Kelly) |
| 1996 |
Cmdr W. L. Herndon (Josef Garcia/Sean Kelly) |
| 1995 |
Roanoke Valley (Cal Beasley/Kirk Andrews) |
| 1994 |
Lord Fairfax (David McDaniel/Doug Churchill) |
| 1993 |
New River (Bruce Johnson/Derrick Fontaine) |
| 1992 |
New River |
| 1991 |
New River |
| 1990 |
New River |
| 1989 |
Occoquan |
| 1988 |
Tidewater |