I don’t honestly know if the Ted Wildman Trophy is the oldest individual award in Ontario college football but it must be among them. It’s been given out since 1932.
From a 1950 report in the Canadian Journal of Comparative Medicine:
The Ted Wildman Trophy was donated by the Harris Abattoir of Toronto to the Ontario Agricultural College Alumni Association, as a memorial to Ted Wildman, a graduate of Class 1922, O.A.C. and an outstanding athlete and student.
Senior students of the two Guelph colleges are eligible for competition for the Trophy. Candidates must satisfy the Trophy Committee on the following points:
1. Proficiency in playing rugby.
2. Conduct on the field of play.
3. Conduct on the campus, in the class room, and in student activities in general.
4. Ability as a leader both on and off the field of play.
5. Ability to co-operate with players, other students and authorities.
6. Academic standing shall be above average.
Ted Wildman was a 1922 graduate of Ontario Agricultural College. He was a multi-sport athlete who excelled in wrestling, boxing and track & field in addition to football. Wildman was a Canadian champion in shotput. Wildman was a member of back-to-back championship football teams at Guelph in 1919 and 1920. His employer, Harris Abattoir of Toronto which later became part of Canada Packers, donated the trophy in his honour after he died at a young age in an automobile accident. Wildman was inducted into the University of Guelph Athletics Hall of Fame in 1986.
The winners of the award:
1932 Sid Henry
1933 George Mills
1934 Ab Folland
1935 Beverly Easton
1936 Hank McDonald
1937 Bill Mitchell
1938 No Award Presented
1939 Ross Chapman
1940 George Reynolds
1941-45 WWII
1946 Burt Matthews
1947 John Harvey
1948 Walter Packman
1949 Jim Baker
1950 Jack Cote
1951 Bob Steckle
1952 Larry Burt
1953 Fraser Kerr
1954 Mark Raithby
1955 Bob Hart
1956 Dave Francis
1957 Bob Billin
1958 Bill Sproule
1959 Bob Keith
1960 John Henry & Don Ward
1961 Dave Hume
1962 Raemond German
1963 Jim MacMillan
1964 Ted Barron
1965 Bruce Groves
1966 Gary Scott
1967 John Vandenberg
1968 Terry Hemming
1969 Steve Stewart
1970 Dave Clarke & Bill Morrison
1971 Don Westlake
1972 Ted McEachern
1973 Greg Scheifele
1974 Dan Cornwell
1975 Bruce Morris
1976 Tom Arnott
1977 Vaughn Wright
1978 Steve Hale
1979 Tim Jewson
1980 Ron Lively
1981 Harry Doering
1982 Scott Hobson
1983 Sam Benincasa
1984 Peter Simpson
1985 John Godry
1986 Mike Knighton
1987 Jim Farrell
1988 Bob McLay
1989 Tom Dimitroff Jr.
1990 Calvin Nigh
1991 Chuck Simms
1992 Dan Walker
1993 Rob Wesseling
1994 Mark Dragich
1995 Kip Wigmore
1996 Ryan Strom
1997 Ian McQueen & Peter Partridge
1998 Joel Varty
1999 Nick Gallo
2000 Jeremy Oxley
2001 Sean Spender
2002 Jonathan Bohnert & Norm Nasser
2003 Mike Dougherty
2004 Andrew Oosterhuis
2005 Adam Carapella
2006 Colin Dyer
2007 Adam Slomer
2008 Graeme Reed
2009 Jeff Cain
2010 Matthew Rossetti
2011 Jedd Gardner [story here]
2012 Zack Androschuck [story here]
2013 Taylor Palmer [story here]
2014 Rob Farquharson [story here]
2015 Patrick McGrath [story here]
2016 Rob Carnegie [story here]
2017 Orion Edwards [story here]
2018 Luke Korol [story here]
2019 Job Reinhart [story here]
The 1940 recipient of this award, George Reynolds passed away on December 10, 2015. He was 99 years old.