Challenge Cup| ROUND | R1 | R2 | R3 | R4 | QF | SF | F | ||
| N | S | N | S | ||||||
| Season archive |
| Northern Section | ||||||
| Tuesday, 13 August 2019 | ||||||
| r2 | East Fife | 0-2 | Stirling Albion | |||
| r2 | Brechin City | 4-5 | Elgin City | |||
| r2 | Montrose | 2-1 | Forfar Athletic | |||
| r2 | Peterhead | 0-0 | Formartine United | p6-7 | ||
| r2 | Brora Rangers | 1-2 | Cove Rangers | |||
| r2 | Hearts B | 3-1 | Cowdenbeath | |||
| r2 | Ross County U20 | 2-3 | Raith Rovers | |||
| Southern Section | ||||||
| Tuesday, 13 August 2019 | ||||||
| r2 | Falkirk | 1-1 | Celtic B | p6-5 | ||
| r2 | Clyde | 4-0 | Motherwell B | |||
| r2 | Stranraer | 0-2 | Rangers B | |||
| r2 | Stenhousemuir | 2-1 | Edinburgh City | |||
| r2 | Dumbarton | 0-1 | St.Mirren U20 | |||
| r2 | Annan Athletic | 1-1 | Kelty Hearts | p5-6 | ||
| r2 | Hamilton U20 | 0-1 | Airdrieonians | |||
| 5 | +3 | Kane HESTER (Elgin City) |
| 3 | +3 | Scott REEKIE (Brechin City) |
| +1 | Aidan KEENA (Hearts B) | |
| 2 | +1 | Mark GALLAGHER (Ross County U20) |
| +2 | Ryan WATTERS (Stenhousemuir) | |
| +2 | Lewis ALLAN (Raith Rovers) | |
| +1 | Josh McPAKE (Rangers B) | |
| Andy WINTER (Hamilton U20) | ||
| +1 | Shane SUTHERLAND (Elgin City) | |
| +1 | Kyle MacLEOD (Brora Rangers) | |
| +1 | Davis KEILLOR-DUNN (Ross County U20) |
