| ROUND | R2 | R3 | R4 | R5 | QF | SF | F | |||||
| r2 | R | r3 | R | r4 | R | r5 | R | qf | R | |||
| Season archive |
| Saturday, 24 November 2018 | |||||
| r3 | Airdrieonians | 3-0 | Dumbarton | ||
| r3 | Morton | 1-1 | Peterhead | ||
| r3 | Berwick Rangers | 1-2 | East Fife | ||
| r3 | Cowdenbeath | 1-0 | Brora Rangers | ||
| r3 | Queen's Park | 0-3 | Raith Rovers | ||
| r3 | Queen of the South | 4-1 | Formartine United | ||
| r3 | Stenhousemuir | 4-2 | Falkirk | ||
| r3 | Forfar Athletic | 2-0 | Broomhill | ||
| r3 | Alloa Athletic | 3-0 | Brechin City | ||
| r3 | Montrose | 0-0 | Annan Athletic | ||
| r3 | Arbroath | 0-1 | Stranraer | ||
| r3 | Fraserburgh | 0-1 | Auchinleck Talbot | ||
| r3 | Beith | 0-3 | Ayr United | ||
| r3 | East Kilbride | 1-0 | Gala Fairydean | ||
| r3 | University of Stirling | 0-4 | Elgin City | ||
| Sunday, 25 November 2018 | |||||
| r3 | Edinburgh City | 1-1 | Inverness CT | ||
| Tuesday, 27 November 2018 | |||||
| r3R | Peterhead | 0-3 | Morton | ||
| r3R | Annan Athletic | 3-4 | Montrose | ||
| Tuesday, 4 December 2018 | |||||
| r3R | Inverness CT | 6-1 | Edinburgh City | ||
| 3 | +3 | Jordan WHITE (Inverness CT) |
| 2 | +2 | Tom WALSH (Inverness CT) |
| Mitchel MEGGINSON (Cove Rangers, 1p) | ||
| +1 | Graham WILSON (Auchinleck Talbot) | |
| +2 | Stephen DOBBIE (Queen of the South) | |
| Paul WILLIS (Berwick Rangers) | ||
| +1 | David COX (Cowdenbeath) | |
| Craig MALCOLM (East Kilbride) | ||
| +2 | Kyle WILKIE (Airdrieonians) | |
| +2 | Conor McBREARTY (Stenhousemuir) | |
| +2 | Aidan SMITH (Annan Athletic, 1p) |