 |
 |
| 1. Round | ||||||
|---|---|---|---|---|---|---|
| 24/04/2021 | 15:00 | Stenhousemuir FC | - | Cowdenbeath FC | 0:2 (0:0) | |
| 15:00 | Albion Rovers | - | Annan Athletic | 1:0 (0:0) | ||
| 2. Round | ||||||
| 27/04/2021 | 19:00 | Annan Athletic | - | Stenhousemuir FC | 1:1 (0:0) | |
| 19:00 | Cowdenbeath FC | - | Brechin City FC | 0:2 (0:1) | ||
| 3. Round | ||||||
| 29/04/2021 | 19:00 | Stenhousemuir FC | - | Albion Rovers | 0:1 (0:1) | |
| 19:00 | Brechin City FC | - | Annan Athletic | 0:3 (0:1) | ||
| 4. Round | ||||||
| 01/05/2021 | 15:00 | Albion Rovers | - | Brechin City FC | 1:1 (0:0) | |
| 15:00 | Annan Athletic | - | Cowdenbeath FC | 1:1 (0:0) | ||
| 5. Round | ||||||
| 04/05/2021 | 19:00 | Cowdenbeath FC | - | Albion Rovers | 2:0 (1:0) | |
| 19:00 | Brechin City FC | - | Stenhousemuir FC | 0:1 (0:0) | ||
