| Period | Club | on loan from | buy option |
|---|---|---|---|
 UWI FC | - | ||
| Rodwood FC | - | ||
| Bull Bay F.C. | - | ||
| Harbour View F.C. (HVFC) | - | ||
| Shortwood FC | - | ||
| Santos Football Club (S.F.C.) | - |
Simon James Bennett - Legend of Clubs
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| Period | Club | on loan from | buy option |
|---|---|---|---|
| UWI FC | - | ||
| Rodwood FC | - | ||
| Bull Bay F.C. | - | ||
| Harbour View F.C. (HVFC) | - | ||
| Shortwood FC | - | ||
| Santos Football Club (S.F.C.) | - |