Challenge Cup| ROUND | R1 | R2 | R3 | R4 | QF | SF | F | |||
| N | r1 | S | N | S | ||||||
| Season archive |
| Tuesday, 1 August 2023 | ||||||
| r1 | St.Mirren U20 | 2-2 | Albion Rovers | p2-4 | ||
| Northern Section | ||||||
| Tuesday, 1 August 2023 | ||||||
| r1 | Brechin City | 2-2 | Hearts B | p5-3 | ||
| r1 | Elgin City | 2-0 | St.Johnstone U20 | |||
| Southern Section | ||||||
| Tuesday, 1 August 2023 | ||||||
| r1 | Spartans | 0-3 | Rangers B | |||
| r1 | Tranent | 0-0 | Motherwell B | p3-1 | ||
| r1 | Kilmarnock U20 | 3-1 | Bonnyrigg Rose | |||
| Northern Section | ||||||
| Wednesday, 2 August 2023 | ||||||
| r1 | Brora Rangers | 1-1 | Aberdeen U20 | p2-4 | ||
| r1 | Dundee B | 4-0 | Buckie Thistle | |||
| r1 | Hibernian U20 | 1-1 | Formartine United | p4-2 | ||
| Southern Section | ||||||
| Wednesday, 2 August 2023 | ||||||
| r1 | University of Stirling | 4-0 | Livingston U20 | |||
| r1 | Celtic B | 1-3 | East Kilbride | |||
| 1 | +1 | Jack WILKIE (Dundee B) |
| +1 | Ben BARRON (Elgin City) | |
| +1 | Robbie FRASER (Rangers B) | |
| +1 | Alieu FAYE (Bonnyrigg Rose) | |
| +1 | Matthew TURNER (St.Mirren U20) | |
| +1 | Arron LYALL (Rangers B) | |
| +1 | Josh LANDERS (Hibernian U20) | |
| +1 | Marc KELLY (East Kilbride) | |
| +1 | Rayan MOHAMMED (Dundee B) | |
| +1 | Makenzie KIRK (Hearts B) | |
| +1 | Euan MUTALE (Dundee B) | |
| +1 | Alex LOWRY (Rangers B) | |
| +1 | Grady McGRATH (Brechin City) | |
| +1 | Ryan MacLEMAN (Elgin City) | |
| +1 | Jordan MacRAE (Brora Rangers) | |
| +1 | Alfie BAVIDGE (Aberdeen U20) | |
| +1 | Rocco FRIEL (Hearts B) | |
| +1 | Steven WARNOCK (Kilmarnock U20) | |
| +1 | Bobby WALES (Kilmarnock U20) | |
| +1 | Rocco VATA (Celtic B) | |
| +1 | Sean FAGAN (Albion Rovers) | |
| +1 | Ethan SUTHERLAND (St.Mirren U20) | |
| +1 | Calum BIGGAR (East Kilbride) | |
| +1 | Niyah JOSEPH (Albion Rovers) | |
| +1 | Max ANDERSON (Dundee B) | |
| +1 | Aaron BROWN (Kilmarnock U20) | |
| +1 | Daniel PARK (Formartine United) | |
| +1 | Fraser MacLEOD (Brechin City) | |
| +1 | Keir SAMSON (East Kilbride) |
