| Période | association | on loan from | buy option |
|---|---|---|---|
 Bears FC | - | ||
 Montego Bay United Football Club | - | ||
| Sporting Central Academy | - | ||
| (ehem.) IM Bears FC | - | ||
 Milltown FC | - | ||
| (ehem.) IM Bears FC | - |
Lesly St. Fleur - Clubs
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| Période | association | on loan from | buy option |
|---|---|---|---|
| Bears FC | - | ||
| Montego Bay United Football Club | - | ||
| Sporting Central Academy | - | ||
| (ehem.) IM Bears FC | - | ||
| Milltown FC | - | ||
| (ehem.) IM Bears FC | - |