| DATE | WoO YEARLY WINNERS |
| 2023 | Brad Sweet (2), Rico Abreu, Brent Marks, Logan Schuchart |
| 2022 | Lance Dewease (3), Brent Marks, Brad Sweet |
| 2021 | Carson Macedo (2), Sheldon Haudenschild, Kyle Larson, Brent Marks, Aaron Reutzel |
| 2020 | David Gravel (2), Donny Schatz, Shane Stewart |
| 2019 | Lance Dewease, David Gravel (2), Brent Marks, Donny Schatz, Tim Shaffer |
| 2018 | Lance Dewease (2), Giovanni Scelzi |
| 2017 | David Gravel (3), Shane Stewart, Brock Zearfoss, Greg Hodnett, James McFadden |
| 2016 | Lance Dewease (2), Daryn Pittman, Danny Dietrich |
| 2015 | Donny Schatz, Danny Dietrich, Stevie Smith (2) |
| 2014 | Daryn Pittman (2), Greg Hodnett, Lance Dewease, David Gravel |
| 2013 | Donny Schatz (2), Don Kreitz Jr., Fred Rahmer |
| 2012 | Fred Rahmer, Steve Kinser, Cody Darrah, Paul McMahan, Donny Schatz |
| 2011 | Daryn Pittman, Greg Hodnett, Jason Meyers (3) |
| 2010 | Chad Layton, Fred Rahmer, Lance Dewease, Greg Hodnett (2), Sammy Swindell |
| 2009 | Greg Hodnett (3), Cody Darrah |
| 2008 | Steve Kinser, Daryn Pittman, Donny Schatz, Cody Darrah |
| 2007 | Donny Schatz (4), Brian Leppo, Chad Layton |
| 2006 | Fred Rahmer, Terry McCarl, Craig Dollansky, Daryn Pittman, Jason Solwald, Doug Esh |
| 2005 | Craig Dollansky, Steve Kinser, Jason Johnson, Paul McMahan, Fred Rahmer (2), Donny Schatz |
| 2004 | Fred Rahmer, Don Kreitz Jr., Lance Dewease, Danny Lasoski, Mark Smith, Donny Schatz |
| 2003 | Don Kreitz Jr., Donny Schatz (3), Steve Kinser |
| 2002 | Steve Kinser, Danny Lasoski, Joey Saldana, Greg Hodnett, Lance Dewease |
| 2001 | Donny Schatz (3), Don Kreitz Jr, Tim Shaffer, Lance Dewease |
| 2000 | Mark Kinser, Fred Rahmer, Lance Dewease, Sammy Swindell, Steve Kinser, Donny Schatz |
| 1999 | Mark Kinser (4), Steve Kinser, Cris Eash |
| 1998 | Mark Kinser (2), Johnny Herrera, Stevie Smith, Kevin Gobrecht |
| 1997 | Sammy Swindell (3), Mark Kinser (3), Jac Haudenschild |
| 1996 | Johnny Herrera, Mark Kinser (2), Steve Kinser (2), Lance Dewease (2) |
| 1995 | Steve Kinser, Dave Blaney, Mark Kinser (3) |
| 1994 | Dave Blaney, Steve Kinser (2), Andy Hillenburg, Sammy Swindell (2), Lance Dewease |
| 1993 | Dave Blaney (2), Don Kreitz Jr. (2), Steve Kinser (2) |
| 1992 | Mark Kinser, Don Kreitz Jr. (2), Steve Kinser (3), Keith Kauffman |
| 1991 | Steve Kinser (3), Sammy Swindell (2), Mark Kinser, Stevie Smith |
| 1990 | Steve Kinser (6), Sammy Swindell |
| 1989 | Bobby Allen (2), Sammy Swindell, Bobby Davis Jr. (2), Stevie Smith (2) |
| 1988 | Bobby Davis Jr (2), Mark Kinser, Cris Eash, Steve Kinser |
| 1987 | Ron Shuman, Steve Kinser (4) |
| 1986 | Doug Wolfgang (2), Bobby Allen (2), Jac Haudenschild |
| 1985 | Keith Kauffman, Sammy Swindell, Doug Wolfgang, Steve Kinser |
| 1984 | Steve Kinser (3), Brad Doty, Sammy Swindell |
| 1983 | Bobby Davis Jr (2), Steve Kinser, Sammy Swindell |
| 1982 | Bobby Allen (2), Sammy Swindell |
| 1981 | Steve Kinser (2) |
| 1980 | Sammy Swindell, Billy Steif, Keith Kauffman |
| 1979 | Lynn Paxton |
| 1978 | Kramer Williamson |
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