| Zeitraum | Verein | Ausgeliehen von | Kaufoption |
|---|---|---|---|
 Red Hills United FC | - | ||
| Olympic Gardens F.C. | - | ||
| Pembroke Hall F.C. | - | ||
| Campro F.C. | - | ||
| Pembroke Hall High School | - |
Shay Don Lee Headley - Transfer-Übersicht
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| Zeitraum | Verein | Ausgeliehen von | Kaufoption |
|---|---|---|---|
| Red Hills United FC | - | ||
| Olympic Gardens F.C. | - | ||
| Pembroke Hall F.C. | - | ||
| Campro F.C. | - | ||
| Pembroke Hall High School | - |