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| Year | Winner | Score | Runner-up |
| 1966 | Guyana | round robin | Trinidad and Tobago |
| 1967 | Trinidad and Tobago | round robin | |
| 1969 | Jamaica | round robin | Bahamas |
| 1973 | Trinidad and Tobago | round robin | |
| 1975 | Jamaica | round robin | Barbados |
| 1977 | Bermuda | round robin | |
| 1979 | Bermuda | round robin | |
| 1981 | Bermuda | round robin | |
| 1983 | Trinidad and Tobago | round robin | |
| 1985 | Trinidad and Tobago | round robin | |
| 1996 | Bermuda | 2020-08-29 00:00:00 | Trinidad and Tobago |
| 1997 | Trinidad and Tobago | 31-14 | Cayman Islands |
| 1998 | Bermuda | round robin | Trinidad and Tobago |
| 1999 | Trinidad and Tobago | round robin | |
| Cayman Islands | | |
| 2001 | Trinidad and Tobago | 23–12 | Bermuda |
| 2005 | Barbados | 52–3 | Bahamas |
| 2008 | Trinidad and Tobago | 40–24 | Guyana |
| 2011 | Bermuda | 11–0 | Guyana |
| 2012 | Bermuda | 18–0 | Guyana |
| 2013 | USA South | 26–18 | Trinidad and Tobago |
| 2014 | Guyana | 30–27 | USA South |
| 2015 | Trinidad and Tobago | 30–16 | Mexico |
| 2016 | Mexico | 32-3 | Guyana |
| 2017 | USA South | 23-19 | Guyana |
| 2018 | USA South | round robin | Cayman Islands |
| 2019 | Bermuda | 33-10 | Guadeloupe |