Cherrey Cup Championship History
The Cherrey Cup was retired following the 2023-24 season as the Midwestern Conference of the GOHL was disbanded with the realignment into two conferences – the West and East.
| Year | Champions | Finalists | Series |
| 2024 | Listowel Cyclones | Stratford Warriors | 4 – 1 |
| 2023 | Stratford Cullitons | Kitchener-Waterloo Siskins | 4 – 2 |
| 2022 | Cambridge Redhawks | Elmira Sugar Kings | 4 – 1 |
| 2021 | Season Cancelled due to COVID Pandemic | ||
| 2020 | Season Cancelled due to COVID Pandemic | ||
| 2019 | Waterloo Siskins | Listowel Cyclones | 4 – 2 |
| 2018 | Listowel Cyclones | Elmira Sugar Kings | 4 – 0 |
| 2017 | Listowel Cyclones | Elmira Sugar Kings | 4 – 2 |
| 2016 | Stratford Cullitons | Waterloo Siskins | 4 – 1 |
| 2015 | Elmira Sugar Kings | Stratford Cullitons | 4 – 1 |
| 2014 | Waterloo Siskins | Stratford Cullitons | 4 – 2 |
| 2013 | Cambridge Winterhawks | Stratford Cullitons | 4 – 1 |
| 2012 | Brantford Golden Eagles | Stratford Cullitons | 4 – 2 |
| 2011 | Elmira Sugar Kings | Listowel Cyclones | 4 – 2 |
| 2010 | Brantford Eagles | Stratford Cullitons | 4 – 2 |
| 2009 | Brantford Eagles | Kitchener Dutchmen | 4 – 1 |
| 2008 | Elmira Sugar Kings | Cambridge Winterhawks | 4 – 2 |
| 2007 | Cambridge Winterhawks | Elmira Sugar Kings | 4 – 0 |
| 2006 | Cambridge Winterhawks | ||
| 2005 | Listowel Cyclones | Owen Sound Greys | 4 – 2 |
| 2004 | Stratford Cullitons | Kitchener Dutchmen | 4 – 2 |
| 2003 | Stratford Cullitons | Kitchener Dutchmen | 4 – 1 |
| 2002 | Elmira Sugar Kings | Stratford Cullitons | 4 – 1 |
| 2001 | Elmira Sugar Kings | Cambridge Winterhawks | 4 – 0 |
| 2000 | Cambridge Winterhawks | Owen Sound Greys | 4 – 2 |
| 1999 | Stratford Cullitons | Cambridge Winterhawks | 4 – 2 |
| 1998 | Elmira Sugar Kings | Stratford Cullitons | 4 – 2 |
| 1997 | Elmira Sugar Kings | Stratford Cullitons | 4 – 3 |
| 1996 | Stratford Cullitons | Owen Sound Greys | 4 – 1 |
| 1995 | Stratford Cullitons | Elmira Sugar Kings | 4 – 0 |
| 1994 | Waterloo Siskins | Cambridge Winterhawks | 4 – 2 |
| 1993 | Kitchener Dutchmen | Stratford Cullitons | 4 – 3 |
| 1992 | Kitchener Dutchmen | Stratford Cullitons | 4 – 1 |
| 1991 | Waterloo Siskins | Stratford Cullitons | 4 – 3 |
| 1990 | Stratford Cullitons | Waterloo Siskins | 4 – 2 |
| 1989 | Waterloo Siskins | Stratford Cullitons | 4 – 2 |
| 1988 | Waterloo Siskins | Elmira Sugar Kings | 4 – 0 |
| 1987 | Stratford Cullitons | Elmira Sugar Kings | 4 – 0 |
| 1986 | Stratford Cullitons | Waterloo Siskins | 4 – 0 |
| 1985 | Waterloo Siskins | Stratford Cullitons | 4 – 1 |
| 1984 | Waterloo Siskins | Stratford Cullitons | 4 – 0 |
| 1983 | Stratford Cullitons | Waterloo Siskins | 4 – 2 |
| 1982 | Stratford Cullitons | Kitchener Ranger B’s | 4 – 2 |
| 1981 | Stratford Cullitons | Kitchener Ranger B’s | 4 – 2 |
| 1980 | Waterloo Siskins | Stratford Cullitons | 4 – 2 |
| 1979 | Stratford Cullitons | Elmira Sugar Kings | 4 – 0 |
| 1978 | Stratford Cullitons | Waterloo Siskins | 4 – 1 |
