| Winners | ||||
|---|---|---|---|---|
| W Connection | 3 | |||
| Joe Public | 2 | |||
| Puerto Rico Islanders | 2 | |||
| Central | 2 | |||
| Portmore United | 2 | |||
| Harbour View | 2 | |||
| San Juan Jabloteh | 1 | |||
| Caledonia AIA | 1 | |||
| Atlético Pantoja | 1 | |||
| Cibao | 1 | |||
| Defence Force | 1 | |||
| United Petrotrin | 1 | |||
| Season | Host | Winners | Score | Runners-up |
| 1997 | United Petrotrin | 2 – 1 | Seba United | |
| 1998 | Joe Public | 1 – 0 | Caledonia AIA | |
| 2000 | Joe Public | -1 | W Connection | |
| 2001 | Defence Force | -2 | W Connection | |
| 2002 | W Connection | -2 | Arnett Gardens | |
| 2003 | San Juan Jabloteh | 2 – 1 1 – 2 (4 – 2 p) | W Connection | |
| 2004 | Harbour View | 1 – 1 2 – 1 | Tivoli Gardens | |
| 2005 | Portmore United | 2 – 1 4 – 0 | Robinhood | |
| 2006 | W Connection | 1 – 0 | San Juan Jabloteh | |
| 2007 | Harbour View | 2 – 1 | Joe Public | |
| 2009 | W Connection | 2 – 1 | Puerto Rico Islanders | |
| 2010 | Puerto Rico Islanders | -1 | Joe Public | |
| 2011 | Puerto Rico Islanders | 3 – 1 | Tempête | |
| 2012 | Caledonia AIA | 1 – 1 (4 – 3 p) | W Connection | |
| Qualified teams | ||||
| 2013 | W Connection (Group 1 winners) | Valencia (Group 2 winners) | ||
| 2014 | Bayamón (Group 1 winners) | Waterhouse (Group 2 winners) | ||
| Season | Host | Winners | Score | Runners-up |
| 2015 | Central | 2 – 1 | W Connection | |
| 2016 | Central | 3 – 0 | W Connection | |
| 2017 | Cibao | 1 – 0 | San Juan Jabloteh | |
| 2018 | Atlético Pantoja | 0 – 0 (6 – 5 p) | Arnett Gardens | |
| 2019 | Kingston, Jamaica | Portmore United Shavar Thomas | Round Robin | Waterhouse |
