Cup Winner
| Season | Team | Title | |
|---|---|---|---|
| 2017 |  | W Connection FC | 5. |
| 2015 |  | Port of Spain | 2. |
| 2014 | | W Connection FC | 4. |
| 2013 |  | Morvant Caledonia United | 3. |
| 2012 | | Morvant Caledonia United | 2. |
| 2011 |  | San Juan Jabloteh | 3. |
| 2009 |  | Joe Public FC | 3. |
FA Cup Trophy
| Season | Team | Title | |
|---|---|---|---|
| 2017 | | W Connection FC | 5. |
| 2015 | | Port of Spain | 2. |
| 2014 | | W Connection FC | 4. |
| 2013 | | Morvant Caledonia United | 3. |
| 2012 | | Morvant Caledonia United | 2. |
| 2011 | | San Juan Jabloteh | 3. |
| 2009 | | Joe Public FC | 3. |