1960's
| 1965 | Dave Lane, Hope |
| 1966 | Ray Cooper, Hope |
| 1967 | Bob Turner, Albion |
| 1968 | Ray Cooper, Hope |
| 1969 | Rudy Vlaardingerbroek, Calvin |
1970's
| 1970 | Craig Cossey, Albion |
| 1971 | Cliff Haverdink, Hope |
| 1972 | Ron Hobday, Olivet |
| 1973 | George Van Kampen, Calvin |
| 1974 | Ben Beversluis, Calvin and Don Harvey, Alma |
| 1975 | Jack McClellan, Albion |
| 1976 | Bob Condon, Olivet |
| 1977 | Jim Lothrop, Alma |
| 1978 | Pat Peregoy, Olivet and Bob Smith, Alma |
| 1979 | Dexter Davis, Albion |
1980's
| 1980 | Pat Peregoy, Olivet |
| 1981 | Tracy Garner, Albion |
| 1982 | James Jackson, Olivet |
| 1983 | Tracy Garner, Albion and Tim Hartson, Albion |
| 1984 | Rob Appell, Hope |
| 1985 | Rob Appell, Hope |
| 1986 | Rob Appell, Hope |
| 1987 | John Dunlop, Albion |
| 1988 | John Dunlop, Albion and Majed Sahouri, Albion |
| 1989 | John Dunlop, Albion |
1990's
| 1990 | Lance Coleman, Albion and John Lumkes, Calvin |
| 1991 | Lance Coleman, Albion and David Sydow, Calvin |
| 1992 | Steve Gilbert, Albion and Thad Karnehm, Calvin |
| 1993 | Steve Gilbert, Albion |
| 1994 | Tom Reason, Albion |
| 1995 | Ray VanArragon, Calvin |
| 1996 | John Stien, Calvin |
| 1997 | John Stien, Calvin |
| 1998 | Dan Ferrucci, Adrian and Steve Michmerhuizen, Calvin |
| 1999 | Phil Sikkenga, Calvin |
2000's
| 2000 | Phil Sikkenga, Calvin |
| 2001 | Phil Sikkenga, Calvin (OR) |
| Joe Kattelus, Hope (OFP) | |
| 2002 | Joel Klooster, Calvin (OR) |
| Mike Palmer, Alma (OFP) | |
| 2003 | Nick Mockeridge, Albion (OR) |
| Nate Meckes, Calvin (OFP) | |
| 2004 | Nick Morgan, Albion (OR) |
| Josh Meckes, Calvin (OFP) | |
| 2005 | Reuben Sportel, Calvin (OR) |
| Nate Meckes, Calvin (OFP) | |
| 2006 | Kelby McClelland, Calvin (OR) |
| Nate Meckes, Calvin (OFP) | |
| 2007 | Ryan TerLouw, Hope (OR) |
| Jason Bowman, Albion (OFP) | |
| 2008 | Russell Dill, Tri-State (OR) |
| Ryan Jensen, Calvin (OFP) | |
| 2009 | Christon Calley, Adrian (OR) |
| Joel Klingenberg, Calvin (OFP) |
2010's
| 2010 | Cameron Lampkin, Hope (OR) |
| Derek Stoll, Adrian (OFP) | |
| 2011 | Nicholas Rinck, Hope (OR) |
| Derek Stoll, Adrian (OFP) | |
| 2012 | Kyle VanderVeen, Hope (OR) |
| Derek Stoll, Adrian (OFP) | |
| 2013 | Tyler Bourdo, Trine (OR) |
| Jacob Mehr, Adrian (OFP) | |
| 2014 | Justin Meredith, Albion (OR) |
| Erik Holstege, Calvin (OFP) | |
| 2015 | Tyler Bourdo, Trine (OR) |
| Erik Holstege, Calvin (OFP) | |
| 2016 | Jordan Davis, Adrian (OR) |
| Austin Rodriguez, Alma (OFP) | |
| 2017 | Patrick Richardville, Trine (OR) |
| Brendan Van Houten, Calvin (OFP) | |
| 2018 | Ethan Valentine, Calvin (OR) |
| Brendan Van Houten (OFP) |
* Beginning in 2001, an award for the outstanding runner and an award for the outstanding field performer was initiated
