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East End Lions FC | 11 | | (1977, 1980, 1985, 1992, 1993, 1994, 1997, 1999, 2005, 2009, 2010) | Mighty Blackpool FC | 10 | | (1968, 1974, 1978, 1979, 1988, 1991, 1996, 1998, 2000, 2001) | Ports Authority FC | 7 | | (1970, 1971, 1972, 1973, 1995, 2008, 2011) | Kallon FC | 4 | | (1982, 1986, 1987, 2006) | Real Republicans FC | 3 | | (1981, 1983, 1984) | Diamond Stars FC | 2 | | (2012, 2013) | Old Edwardians FC | 1 | | (1990) | Freetown City FC | 1 | | (1989) |
| Mighty Blackpool FC | 4 |
| (1983, 1988, 1994, 2000) | | Kamboi Eagles FC | 3 |
| (1981, 1985, 2014) | | East End Lions FC | 3 |
| (1973, 1980, 1989) | | Old Edwardians FC | 2 |
| (1984, 2001) | | Ports Authority FC | 2 |
| (1990, 1991) | | Bai Bureh Warriors FC | 2 |
| (1978, 1982) | | Kallon FC | 1 |
| (2007) | | Diamond Stars FC | 1 |
| (1992) | | Real Republicans FC | 1 |
| (1986) | | Wusum Stars FC | 1 |
| (1979) |
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