Challenge Cup| ROUND | R1 | R2 | R3 | R4 | QF | SF | F | |||
| N | r1 | S | N | S | ||||||
| Season archive |
| Northern Section | ||||||
| Tuesday, 15 August 2023 | ||||||
| r2 | Brechin City | 0-4 | Hibernian U20 | |||
| r2 | Elgin City | 0-0 | Forfar Athletic | p4-3 | ||
| r2 | Aberdeen U20 | 3-5 | Peterhead | |||
| r2 | Dundee B | 0-0 | East Fife | p3-5 | ||
| Southern Section | ||||||
| Tuesday, 15 August 2023 | ||||||
| r2 | Stirling Albion | 0-3 | East Kilbride | |||
| r2 | Stenhousemuir | 1-2 | Rangers B | |||
| r2 | Albion Rovers | 2-0 | Tranent | |||
| r2 | Annan Athletic | 3-1 | Stranraer | |||
| Wednesday, 16 August 2023 | ||||||
| r2 | Clyde | 1-3 | University of Stirling | |||
| r2 | Kilmarnock U20 | 1-1 | Dumbarton | p8-9 | ||
| 3 | +2 | Niyah JOSEPH (Albion Rovers) |
| 2 | +1 | Marc KELLY (East Kilbride) |
| +2 | Jordon BROWN (Peterhead) | |
| +1 | Alfie BAVIDGE (Aberdeen U20) | |
| +1 | Bobby WALES (Kilmarnock U20) |
