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| 01.08.2023 | 20:30 | Elgin City | - | St. Johnstone FC (R) | 2:0 (1:0) | |
| 20:30 | Brechin City FC | - | Heart of Midlothian (R) | 5:3 (2:0, 2:2) i.E. | ||
| 20:30 | St. Mirren FC (R) | - | Albion Rovers | 2:4 (0:2, 2:2) i.E. | ||
| 20:45 | Tranent Juniors | - | Motherwell FC (R) | 3:1 (0:0, 0:0) i.E. | ||
| 20:45 | The Spartans FC | - | Rangers FC (R) | 0:3 (0:1) | ||
| 20:45 | Kilmarnock FC (R) | - | Bonnyrigg Rose Athletic | 3:1 (2:0) | ||
| 02.08.2023 | 20:30 | Hibernian FC (R) | - | Formartine United | 4:2 (1:1, 1:1) i.E. | |
| 20:45 | Brora Rangers FC | - | Aberdeen FC (R) | 2:4 (1:0, 1:1) i.E. | ||
| 20:45 | University of Stirling FC | - | Livingston FC (R) | 4:0 (1:0) | ||
| 20:45 | Celtic FC (R) | - | East Kilbride FC | 1:3 (1:1) | ||
| 21:00 | Dundee FC (R) | - | Buckie Thistle | 4:0 (3:0) |
