| Club | Nombre de titres | Années |
|---|
| Kensington Rovers | 12 | 1910, 1911, 1912, 1914, 1915, 1916, 1917, 1918, 1919, 1921, 1922, 1934 |
| Weymouth Wales FC | 12 | 1967, 1969, 1970, 1972, 1975, 1984, 1987, 2011, 2014, 2016, 2017, 2019 |
| Notre Dame SC | 6 | 1982, 1996, 1999, 2000, 2003, 2005 |
| Paradise FC | 6 | 1996, 1999, 2000, 2003, 2005, 2018 |
| Everton | 5 | 1947-1948, 1960, 1962, 1986, 1990 |
| Empire | 4 | 1924, 1925, 1926, 1928 |
| Pride of Gall Hill FC | 4 | 1924, 1925, 1926, 1928 |
| Harrison College | 4 | 1912, 1913, 1920, 1923 |
| Barbados Defense Force | 3 | 1994, 2012, 2015 |
| Spartan | 3 | 1927, 1949, 1950 |
| Youth Milan FC | 2 | 2002, 2009 |
| Carlton | 1 | 1952 |
| Pinelands | 1 | 1989 |
| Brittons Hill FC | 1 | 2007 |
| Rendezvous FC | 1 | 2013 |
