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Preliminary Round 1
Preliminary Round 2
Round 1
Round 2
Round 3
Round 4
Round 5
Quarterfinal
Semifinal
Final
| 25.09.2023 | |||
| 20:05 | Stirling University | 1-3 | Albion Rovers |
| 24.09.2023 | |||
| 15:00 | Broomhill FC | 3-1 | Cumbernauld Colts |
| 23.09.2023 | |||
| 16:00 | Banks O' Dee | 6-0 | Dalbeattie Star |
| 16:00 | Bo'ness United | 3-0 | Darvel FC |
| 16:00 | Brechin City | 4-0 | Rothes FC |
| 16:00 | Brora Rangers | 5-1 | Berwick Rangers |
| 16:00 | Broxburn Athletic | 2-1 | Nairn County |
| 16:00 | Caledonian Braves | 1-2 | Fraserburgh FC |
| 16:00 | Camelon Juniors | 1-2 | Civil Service Strollers |
| 16:00 | Clachnacuddin | 1-0 | Inverurie Loco Works |
| 16:00 | Cowdenbeath | 2-1 AET | Linlithgow Rose |
| 16:00 | Dalkeith Thistle FC | 0-7 | Clydebank FC |
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