What follows is the list of top teams, MVPs, Pitchers of the Year, Managers of the Year, batting champions, and ERA champs for each Valley League season from 1994 to 2021. This information is as complete as possible; some years the league did not name a Pitcher of the Year, and other seasons no Manager or Coach of the Year was named. The batting and ERA champ are listed only if the league officially recognized them.
2021
- Playoff Champion- Strasburg (Defeated Waynesboro two games to zero)
- Regular Season Title- Charlottesville (30-10)
- MVP- Austin Bulman, Winchester
- Pitcher of the Year- Reed Mascolo, New Market
- Manager of the Year- Kory Koehler, Charlottesville
2019
- Playoff Champion- Charlottesville (Defeated Strasburg two games to zero)
- Regular Season Title- Waynesboro (31-11)
- MVP- Aidan Nagle, Woodstock
- Pitcher of the Year- Tristen Bayless, Woodstock
- Manager of the Year- Zac Cole, Waynesboro
2018
- Playoff Champion- New Market (Defeated Charlottesville two games to zero)
- Regular Season Title- Covington (26-16)
- MVP- Andrew Eyster, New Market
- Pitcher of the Year- Jared Wetherbee, Charlottesville
- Manager of the Year- Alex Kotheimer, Covington
2017
- Playoff Champion- Charlottesville (Defeated Strasburg two games to one)
- Regular Season Title- Charlottesville (32-10)
- MVP- Michael Wielansky, Charlottesville
- Pitcher of the Year- Thomas Sutera, Purcellville
- Manager of the Year- Corey Hunt, Charlottesville
2016
- Playoff Champion- Strasburg (Defeated Waynesboro two games to zero)
- Regular Season Title- Strasburg and Waynesboro (30-12)
- MVP- Zach Sterry, Waynesboro
- Pitcher of the Year- Erne Valdes, Front Royal
2015
- Playoff Champion- Strasburg (Defeated Staunton two games to one)
- Regular Season Title- Staunton and Harrisonburg (29-13) (Staunton won one game playoff for overall top seed)
- MVP- Shane Billings, Harrisonburg
- Pitcher of the Year- Hayden McCutcheon, Charlottesville
2014
- Playoff Champion- Waynesboro (Defeated Charles Town two games to one)
- Regular Season Title- Harrisonburg (29-13)
- MVP- Gunnar McNeill, Staunton
- Pitcher of the Year- Jake Harper, Front Royal
2013
- Playoff Champion- Waynesboro (Defeated Strasburg two games to one)
- Regular Season Title- Harrisonburg (32-12)
- MVP- Jordan Tarsovich, Strasburg
- Pitcher of the Year- Justin Camp, Harrisonburg
- Manager of the Year- Phil Betterly, Woodstock
2012
- Playoff Champion- Harrisonburg (Defeated Winchester three games to one)
- Regular Season Title- Winchester and Waynesboro (31-13)
- MVP- Julian Ridings, Waynesboro
2011
- Playoff Champion- Covington (Defeated Rockbridge two games to one)
- Regular Season Title- Harrisonburg (32-12)
- MVP- Brad Zebedis. Strasburg
2010
- Playoff Champion- Luray (Defeated Front Royal two games to zero)
- Regular Season Title- Haymarket (30-14)
- MVP- Cory Spangenberg, Winchester
2009
- Playoff Champion- Haymarket (Defeated Covington three games to one)
- Regular Season Title- Front Royal (29-15)
- MVP- Greg Hopkins, Haymarket
2008
- Playoff Champion- Luray (Defeated Covington three games to zero)
- Regular Season Title- Luray and Waynesboro (30-14)
- MVP- Tyler Townsend, Winchester
- Coach of the Year- Lawrence Nesselrodt, Waynesboro
2007
- Playoff Champion- Waynesboro (Defeated Luray four games to one)
- Regular Season Title- Waynesboro (30-14-1)
- MVP- Luke Greinke, Winchester
2006
- Playoff Champion- Luray (Defeated Staunton three games to two)
- Regular Season Title- New Market (32-10)
- MVP- Tyler Kuhn, Luray
2005
- Playoff Champion- Covington (Defeated New Market two games to one)
- Regular Season Title- Luray (30-14)
- MVP- Daniel Murphy, Luray
2004
- Playoff Champion- Winchester (Defeated Staunton two games to zero)
- Regular Season Title- Harrisonburg (30-14)
- MVP- Jon Love, Front Royal, and Jeremy Terni, Winchester
- Batting Champion- Joe Kemp, Harrisonburg
- ERA Champion- Mike Wagner, Winchester
2003
- Playoff Champion- Winchester (Defeated New Market three games to two)
- Regular Season Title- Winchester (38-12)
- MVP- Jeff Van Houten, Harrisonburg
- Batting Champion- Jeff Van Houten, Harrisonburg
- ERA Champion- Phil Bartleski, New Market
- Manager of the Year- Jason Johnson, Winchester
2002
- Playoff Champion- New Market (Defeated Covington three games to one)
- Regular Season Title- Covington (26-14)
- MVP- Jon Honce, Covington
- Batting Champion- Justin Morgan, Luray
- ERA Champion- Taylor Cobb, Staunton
- Coach of the Year- Bob Wease, Harrisonburg
2001
- Playoff Champion- Winchester (Defeated Covington three games to two)
- Regular Season Title- Winchester (28-12)
- MVP- Wes Timmons, Winchester
- Hitting Award- Wes Timmons, Winchester
- Pitching Award- Chris Kees, Winchester
- Coach of the Year- Joe McNamee, Covington
2000
- Playoff Champion- Harrisonburg (Defeated Staunton three games to one)
- Regular Season Title- Staunton (28-12)
- MVP- Joe Hastings, Staunton
- Hitting Award- Chris Durbin, Harrisonburg
- Pitching Award- BJ Benik, Front Royal
1999
- Playoff Champion- Staunton (Defeated Winchester three games to zero)
- Regular Season Title- Staunton (27-13)
- MVP- Ernie Durazo, Harrisonburg
- Hitting Award- Kevin Olkowski, Waynesboro
- Pitching Award- Carl Rowland, Winchester
1998
- Playoff Champion- Waynesboro (Defeated Staunton three games to zero)
- Regular Season Title- Staunton (24-16)
- MVP- Jon Rauch, Harrisonburg
- Hitting Award- Nate Rewers, Front Royal
- Pitching Award- Jon Rauch, Harrisonburg
1997
- Playoff Champion- Winchester (Defeated Front Royal- forfeit)
- Regular Season Title- Staunton (26-14)
- MVP- Nate Rewers, Front Royal
1996
- Playoff Champion- Staunton (Defeated Harrisonburg three games to one)
- Regular Season Title- Waynesboro (28-12)
- MVP- Bill Eaton, Waynesboro
1995
- Playoff Champion- Staunton (Defeated Waynesboro three games to zero)
- Regular Season Title- Staunton (29-11)
- MVP- Jason Michaels, Staunton
1994
- Playoff Champion- New Market (Defeated Harrisonburg three games to two)
- Regular Season Title- Staunton (26-14)
- MVP- Darren Hayes, New Market
Thanks to Jim Phillips and Bruce Alger for much of the information; Chaz Weaver’s The Valley Baseball League was also consulted.