| ROUND | R1 | R2 | R3 | R4 | QF | SF | F | |||
| N | r1 | S | N | S | ||||||
| Season archive | 
| Saturday, 14 October 2023 | ||||||
| r4 | Raith Rovers | 3-1 | Montrose | |||
| 32 | Smith | 72 | Watson | |||
| 57 | Easton | |||||
| 67 | Mullin | |||||
| r4 | Falkirk | 1-0 | Queen's Park | |||
| 6(p) | Allan | |||||
| r4 | Morton | 4-1 | Kelty Hearts | |||
| 3 | Muirhead | 12 | Lyon | |||
| 55 | Muirhead | |||||
| 63 | Muirhead | |||||
| 69 | Crawford | |||||
| r4 | Queen of the South | 1-2 | Arbroath | |||
| 12 | Doherty | 54 | Bird | |||
| 90 | McKenna | |||||
| r4 | The New Saints | 2-2 | East Fife | p5-4 | ||
| 14 | Young | 35 | Trouten | |||
| 76(p) | Brobbel | 60 | McManus | |||
| r4 | Peterhead | 0-2 | Dundee United | |||
| 7 | Middleton | |||||
| 71 | Watt | |||||
| r4 | East Kilbride | 2-5 | Hamilton | |||
| 31 | McGowan | 17 | Mumbongo | |||
| 53 | Flanagan | 20(og) | Arnott | |||
| 36(p) | MacDonald | |||||
| 38 | Murray | |||||
| 80 | MacDonald | |||||
| Tuesday, 7 November 2023 | ||||||
| r4 | Rangers B | 2-4 | Airdrieonians | |||
| 5 | Gentles | 11 | Gallagher | |||
| 62 | Dowell | 22 | McGill | |||
| 54 | McGill | |||||
| 90+1 | McCabe | |||||
| 4 | Niyah JOSEPH (Albion Rovers) | |
| +3 | Robbie MUIRHEAD (Morton) | |
| 2 | Botti BIA-BI (Kelty Hearts) | |
| Jordon BROWN (Peterhead) | ||
| +1 | Nathan FLANAGAN (East Kilbride) | |
| Keir SAMSON (East Kilbride) | ||
| Andy McCARTHY (Peterhead) | ||
| +2 | Kyle MacDONALD (Hamilton) | |
| +2 | Gabby McGILL (Airdrieonians) | |
| Marc KELLY (East Kilbride) | ||
| Kieran SHANKS (Peterhead) | ||
| +1 | Rhys McCABE (Airdrieonians) | |
| Arron LYALL (Rangers B) | ||
| +1 | Reece LYON (Kelty Hearts) | |
| Alfie BAVIDGE (Aberdeen U20) | ||
| Bobby WALES (Kilmarnock U20) | ||
| +1 | Brad YOUNG (The New Saints) | |
| +1 | Connor McMANUS (East Fife) |