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| H | Montrose FC | - | Greenock Morton FC | 2:1 (0:1) | ||
| R | Greenock Morton FC | - | Montrose FC | 3:1 (2:1, 2:1) n.V. | ||
| H: 08.05.2021 16:00 | R: 11.05.2021 20:45 | Sieger: Greenock Morton FC | ||||
| H | Cove Rangers | - | Airdrieonians FC | 1:1 (0:0) | ||
| R | Airdrieonians FC | - | Cove Rangers | 3:2 (1:1, 2:2) n.V. | ||
| H: 08.05.2021 16:00 | R: 11.05.2021 20:45 | Sieger: Airdrieonians FC | ||||
