Campeón
| Temporada | Equipo | Título | |
|---|---|---|---|
| 2016 |  | Police FC Montserrat | 6. |
| 2004 |  | Ideal FC | 1. |
| 2003 | | Police FC Montserrat | 5. |
| 2001 | | Police FC Montserrat | 4. |
| 2000 | | Police FC Montserrat | 3. |
| 1996 | | Police FC Montserrat | 2. |
| 1974 | | Police FC Montserrat | 1. |
Championship
| Temporada | Equipo | Título | |
|---|---|---|---|
| 2016 | | Police FC Montserrat | 6. |
| 2004 | | Ideal FC | 1. |
| 2003 | | Police FC Montserrat | 5. |
| 2001 | | Police FC Montserrat | 4. |
| 2000 | | Police FC Montserrat | 3. |
| 1996 | | Police FC Montserrat | 2. |
| 1974 | | Police FC Montserrat | 1. |