Teams Hesketh Benjamin played for
| Main FC | Leeward Islands (1964/65-1968/69) |
| Combined Leeward and Windward Islands (1965/66) | |
| West Indies Competition | Combined Leeward and Windward Islands (1965/66) |
| Leeward Islands (1966/67-1968/69) | |
| Miscellaneous | St Kitts Combined Clubs (1969/70) |
| St Kitts (1970-1974) |
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