Past Winners of the cross-country I-500, with brands.
- 1966 Herb Howe (Polaris)
- 1967 Gerry Reese (Polaris)
- 1968 Dale Cormican (Arctic Cat)
- 1969 Dale Cormican (Arctic Cat)
- 1970 LeRoy Lindblad (Polaris)
- 1971 LeRoy Lindblad (Polaris)
- 1972 Yvon DuHamel (Ski-Doo)
- 1973 Stan Hayes (Polaris)
- 1974 Marv Ode (Arctic Cat)
- 1975 Ed Monsrud (Polaris)
- 1976 Brian Nelson (John Deere)
- 1977 Archie Simonson (Polaris)
- 1978 Brian Nelson (Arctic Cat)
- 1979 Paul Matejka (Polaris)
- 1980 Bruce Olson (Polaris)
- 1987 Nolan Knockenmus (Polaris)
- 1988 Lauren Wolff (Polaris)
- 1989 Jeremy Fyle (Polaris)
- 1990 Kirk Hibbert (Arctic Cat)
- 1991 Jack Struthers (Polaris)
- 1992 Jack Struthers (Polaris)
- 1993 Kirk Hibbert (Arctic Cat)
- 1994 Jack Struthers (Polaris)
- 1995 Brad Pake (Arctic Cat)
- 1996 Brad Pake (Arctic Cat)
- 1997 Corey Davidson (Polaris)
- 1998 Todd Wolff (Ski-Doo)
- 1999 Todd Wolff (Ski-Doo)
- 2000 Bryan Dyrdahl (Arctic Cat)
- 2001 Troy Taggart (Arctic Cat)
- 2002 cancelled
- 2003 Corey Davidson (Polaris)
- 2004 Bryan Dyrdahl (Ski-Doo)
- 2005 Corey Davidson (Polaris)
- 2006 Bryan Dyrdahl (Ski-Doo)
- 2007 Ross Erdman (Ski-Doo)
- 2008 Bryan Dyrdahl (Ski-Doo)
- 2009 Bryan Dyrdahl (Ski-Doo)
- 2010 Dan Ebert (Arctic Cat)
- 2011 Brian Dick (Arctic Cat)
- 2012 cancelled
- 2013 Ryan Simons (Arctic Cat)
- 2014 Brian Dick (Arctic Cat)
- 2015 Cancelled
- 2016 Cancelled
- 2017 Zach Herfindahl (Arctic Cat)
- 2018 Aaron Christensen (Polaris)
- 2019 Zach Herfindahl (Arctic Cat)
- 2020 Zach Herfindahl (Arctic Cat)
- 2021 Cancelled
- 2022 Zach Herfindahl (Arctic Cat)
- 2023 Zach Herfindahl (Arctic Cat)
- 2024 Cancelled
- 2025 Cancelled
