Challenge Cup| ROUND | R1 | R2 | R3 | R4 | QF | SF | F | ||
| N | S | N | S | ||||||
| Season archive |
| Northern Section | ||||||
| Tuesday, 6 August 2019 | ||||||
| r1 | Albion Rovers | 1-4 | Hearts B | |||
| r1 | Fraserburgh | 2-3 | Ross County U20 | |||
| r1 | Brora Rangers | 6-0 | Aberdeen U20 | |||
| r1 | St.Johnstone U20 | 1-4 | Cove Rangers | |||
| r1 | Hibernian U20 | 3-4 | Elgin City | |||
| r1 | Livingston U20 | 1-3 | Formartine United | |||
| Southern Section | ||||||
| Tuesday, 6 August 2019 | ||||||
| r1 | Berwick Rangers | 1-2 | Rangers B | |||
| r1 | Queen's Park | 2-2 | Celtic B | p3-4 | ||
| r1 | Kelty Hearts | 4-0 | Kilmarnock U20 | |||
| r1 | St.Mirren U20 | 1-0 | East Kilbride | |||
| Wednesday, 7 August 2019 | ||||||
| r1 | Hamilton U20 | 4-0 | Broomhill | |||
| r1 | Motherwell B | 1-0 | Spartans | |||
| 2 | +2 | Kane HESTER (Elgin City) |
| +2 | Andy WINTER (Hamilton U20) | |
| +2 | Aidan KEENA (Hearts B) |
