| ROUND | R2 | R3 | R4 | R5 | QF | SF | F | |||||
| r2 | R | r3 | R | r4 | R | r5 | R | qf | R | |||
| Season archive |
| Saturday, 20 October 2018 | |||||
| r2 | Berwick Rangers | 3-1 | Gretna | ||
| r2 | Cowdenbeath | 2-1 | Clyde | ||
| r2 | Stirling Albion | 1-2 | Queen's Park | ||
| r2 | Albion Rovers | 0-2 | Formartine United | ||
| r2 | Peterhead | 3-2 | Kelty Hearts | ||
| r2 | Elgin City | 2-0 | Whitehill Welfare | ||
| r2 | Edinburgh City | 1-0 | Civil Service Strollers | ||
| r2 | Deveronvale | 1-2 | University of Stirling | ||
| r2 | Cove Rangers | 1-1 | Auchinleck Talbot | ||
| r2 | Gala Fairydean | 2-0 | East Stirlingshire | ||
| r2 | Brora Rangers | 6-0 | Coldstream | ||
| r2 | Beith | 4-0 | Linlithgow Rose | ||
| r2 | East Kilbride | 3-1 | Spartans | ||
| r2 | Cumbernauld Colts | 1-4 | Broomhill | ||
| r2 | Rothes | 0-1 | Annan Athletic | ||
| r2 | Caledonian Braves | 1-2 | Fraserburgh | ||
| Saturday, 27 October 2018 | |||||
| r2R | Auchinleck Talbot | 2-1 | Cove Rangers | ||
| 2 | +2 | Mitchel MEGGINSON (Cove Rangers, 1p) |
| +2 | Paul WILLIS (Berwick Rangers) | |
| +2 | Craig MALCOLM (East Kilbride) |