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Preliminary Round 1
Preliminary Round 2
Round 1
Round 2
Round 3
Round 4
Round 5
Quarterfinal
Semifinal
Final
| 02.09.2023 | |||
| 20:30 | Fort William | 1-10 | Clydebank FC |
| 16:00 | Creetown FC | 1-3 | Whitehill Welfare |
| 16:00 | Cumnock Juniors FC | 1-0 | Girvan FC |
| 16:00 | Dunbar United FC | 4-2 | Vale of Leithen |
| 16:00 | Hawick Royal Albert | 1-2 | Golspie Sutherland |
| 16:00 | Hill of Beath FC | 0-1 | Tayport FC |
| 16:00 | Irvine Meadow XI FC | 1-2 | Dunipace FC |
| 16:00 | Musselburgh Athletic | 6-0 | Coldstream FC |
| 16:00 | Newton Stewart | 1-4 | Luncarty FC |
| 16:00 | Pollok FC | 2-2/p.3-0 | Benburb FC |
| 16:00 | Preston Athletic | 0-0/p.3-4 | Dundonald Bluebell |
| 16:00 | Sauchie Juniors FC | 4-0 | Burntisland Shipyard AFC |
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