| Scottish Challenge Cup26/27 Actual |  Clydebank FC |
| Scottish Challenge Cup25/26 |  Inverness CT |
| Scottish Challenge Cup24/25 |  Livingston |
| Scottish Challenge Cup23/24 |  Airdrieonians |
| Scottish Challenge Cup22/23 |  Hamilton |
| Scottish Challenge Cup21/22 |  Raith |
| Scottish Challenge Cup19/20 | |
| Scottish Challenge Cup19/20 | |
| Scottish Challenge Cup18/19 |  Ross County |
| Scottish Challenge Cup17/18 | Inverness CT |
| Scottish Challenge Cup16/17 |  Dundee Utd |
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