1967–68 Toronto Young Nats

1968–69 Toronto Shopsy’s

1969–70 Sudbury

1970–71 Toronto Shopsy’s

1971–72 Toronto Shopsy’s 

1972–73 Don Valley

1973–74 Toronto Young Nats

1974–75 Toronto Shopsy’s

1975–76 – No Series –

1976–77 Wexford

1977–78 Nepean

1978–79 Toronto Shopsy’s

1979–80 Thunder Bay

1980–81 Toronto Red Wings

1981–82 Mississauga Reps

1982–83 Toronto Marlboros

1983–84 Mississauga Reps

1984–85 Toronto Young Nats

1985–86 Wexford

1986–87 Gloucester

1987–88 Mississauga Reps

1988–89 Toronto Red Wings

1989–90 Mississauga Hawks

1990–91 Toronto Marlboros

1991–92 Wexford

1992–93 Toronto Red Wings

1993–94 Toronto Red Wings

1994–95 Wexford

1995–96 Toronto Red Wings

1996–97 Richmond Hill

1997–98 Toronto Marlboros

1998–99 North York Canadiens

1999–00 Toronto Marlboros

2000–01 Toronto Jr. Canadiens

2001–02 Toronto Jr. Canadiens

2002–03 Vaughan Kings

2003–04 Niagara Falls Thunder

2004–05 Toronto Jr. Canadiens

2005–06 Toronto Marlboros

2006–07 York Simcoe Express

2007–08 Toronto Red Wings

2008–09 York Simcoe Express

2009–10 Toronto Marlboros

2010–11 Hamilton Jr. Bulldogs

2011–12 Quinte Red Devils

2012–13 Mississauga Rebels

2013–14 London Jr. Knights

2014–15 Toronto Marlboros

2015-16 Don Mills Flyers

2016–17 Toronto Jr. Canadiens

2017-18 Sun County Panthers

2018-19 Mississauga Senators