| Period | Club | on loan from | buy option |
|---|---|---|---|
 St. Bess FC | - | ||
| Cavalier FC | - | ||
| Tivoli Gardens F.C. | - | ||
| Tafari Lions F.C. | Tivoli Gardens F.C. | ||
| Tivoli Gardens F.C. | - | ||
| Harbour View F.C. (HVFC) | - |
Roybert Jameel Clarke - Legend of Clubs
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| Period | Club | on loan from | buy option |
|---|---|---|---|
| St. Bess FC | - | ||
| Cavalier FC | - | ||
| Tivoli Gardens F.C. | - | ||
| Tafari Lions F.C. | Tivoli Gardens F.C. | ||
| Tivoli Gardens F.C. | - | ||
| Harbour View F.C. (HVFC) | - |