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| 15/08/2023 | 19:30 | Brechin City FC | - | Hibernian FC (R) | 0:4 (0:2) | |
| 19:45 | Annan Athletic | - | Stranraer FC | 3:1 (1:1) | ||
| 19:45 | Elgin City | - | Forfar Athletic | 4:3 (0:0, 0:0) pso | ||
| 19:45 | Aberdeen FC (R) | - | Peterhead FC | 3:5 (1:0) | ||
| 19:45 | Dundee FC (R) | - | East Fife FC | 3:5 (0:0, 0:0) pso | ||
| 19:45 | Stirling Albion FC | - | East Kilbride FC | 0:3 (0:1) | ||
| 19:45 | Albion Rovers | - | Tranent Juniors | 2:0 (0:0) | ||
| 19:45 | Stenhousemuir FC | - | Rangers FC (R) | 1:2 (0:0) | ||
| 16/08/2023 | 19:45 | Kilmarnock FC (R) | - | Dumbarton FC | 8:9 (0:1, 1:1) pso | |
| 19:45 | Clyde FC | - | University of Stirling FC | 1:3 (0:1) |
