1983/1984 Cowichan
Olympics Div 3
1984/1985 Sagres
FC
1985/1986 UVic
Norsemen
1986/1987 Oak Bay
Alumni Over 30
1987/1988 Victoria
West Over 30
1988/1989 Gordon
Head Div 3
1989/1990 Victoria
Athletics Over 30
1990/1991 Victoria
Athletics Div 3
1991/1992 Victoria
West Over 30
1992/1993 ` Castaways Div 3
1993/1994 Victoria
West Over 30
1994/1995 Victoria
West Over 30
1995/1996 Victoria
Athletics Over 30
1996/1997 Victoria
City Div 4
1997/1998 Victoria
Athletics Over 30
1998/1999 Victoria
Athletics Over 31
This was the last year that Masters aged teams participated in the Challenge Cup. The new Tony Grover Cup was initiated for all teams in Masters.
1999/2000 Saltspring
FC Div 3
2000/2001 Cordova
Bay United Div 3
2001/2002 Saltspring
United Div 3
2002/2003 Vantreights
FC
2003/2004 Genesis
FC
2004/2005 Gorge
FC Div 3
2005/2006 Prospect
Lake Lakers Black
2006/2007 Shell
Beach Raiders Div 4
2007/2008 Gorge
FC Div 4
2008/2009 Sagres
FC Div 3
2009/2010 Vic
West Spurs Div 3
2010/2011 Vic
West Spurs Div 3
2011/2012 Gordon Head Active Earth Engineering
2012/2013 Campbell
River Golden Wings
2013/2014 Vantreights
FC
2014/2015 Alberni
Athletics
2015/2016 Juan de
Fuca Div 3
2016/2017 Mid
Isle Mariners
2017/2018 Gorge
Us-Guys
2018/2019 Gorge Us-Guys
2019/2020 Vantreights FC
2020/2021 COVID-19
2021/2022 ?????
