Cup Winners
| Temporada | Clube | |
| 2012/2013 |  | Morvant Caledonia United |
| 2011/2012 | | Morvant Caledonia United |
| 2007/2008 | | Morvant Caledonia United |
| 2002/2003 |  | North East Stars |
| 2001/2002 |  | W Connection |
| 1999/2000 | | W Connection |
| 1998/1999 | | W Connection |
| 1995/1996 |  | Defence Force |
| 1990/1991 | | Defence Force |
| 1988/1989 | | Defence Force |
| 1984/1985 | | Defence Force |
| 1980/1981 | | Defence Force |
| 1973/1974 | | Defence Force |
| 1937/1938 |  | Floriana |