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 Gorge Us-Guys

2022/2023

2023/2024 Vic West Div 4

2024/2025 ?