| Zeitraum | Verein | Ausgeliehen von | Kaufoption |
|---|---|---|---|
 Crystal Palace FC | Chelsea London FC | ||
| Chelsea London FC | - | ||
| Leicester City | - | ||
| Huddersfield Town FC | Leicester City | ||
| Leicester City | - | ||
| Leicester City Football Club Youth Academy | - | ||
| (ehem.) Rushden & Diamonds Juniors FC | - | ||
| Bletchley Youth | - | ||
| Redborne Upper School | - | ||
| Woburn Lions Youth | - |
Benjamin James Chilwell - Transfer-Übersicht
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