| Data | Ora | Casa | Trasferta | Fase | Edizione | ||||
|---|---|---|---|---|---|---|---|---|---|
| 2023-11-25 | 16:00 | Annan Athletic |  | 4-5(d.t.s.) |  | Dumbarton | 3T | ||
| 2023-09-09 | 16:00 | Annan Athletic | | 0-2 |  | Peterhead FC | 3T | ||
| 2023-08-15 | 20:45 | Annan Athletic | | 3-1 |  | Stranraer | 1T | ||
| 2023-08-15 | 20:45 | Annan Athletic | | 3-1 | | Stranraer | 2T | ||
| 2023-07-29 | 16:00 | Annan Athletic | | 2-3 |  | Raith Rovers | GrpF |
