| Zeitraum | Verein | Ausgeliehen von | Kaufoption |
|---|---|---|---|
 Rae Town F.C. | - | ||
 Toronto FC | - | ||
 Coastal Carolina Chanticleers (Coastal Carolina University) | - | ||
| Cincinnati State Surge (Cincinnati State Technical and Community College) | - | ||
| Portmore United F.C. | - | ||
| Garvey Maceo High School | - | ||
| Portmore United F.C. | - |
Ashton Bennett - Transfer-Übersicht
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