| Period | Club | on loan from | buy option |
|---|---|---|---|
 O'Leary Soccer Academy Edmonton | - | ||
 (ehem.) Orange County Blues FC | - | ||
 Kilmarnock FC | - | ||
| Vancouver Whitecaps FC | Kilmarnock FC | ||
| Kilmarnock FC | - | ||
| Dundee Football Club | Kilmarnock FC | ||
| Kilmarnock FC | - | ||
| Aberdeen FC | - |
Ryan O'Leary - Clubs
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