Challenge Cup| ROUND | R1 | R2 | R3 | QF | SF | F | ||
| N | S | N | S | |||||
| Season archive |
| Northern Section | ||||||
| Saturday, 4 September 2021 | ||||||
| r2 | Raith Rovers | 1-0 | Forfar Athletic | |||
| r2 | Cowdenbeath | 0-2 | Alloa Athletic | |||
| r2 | Inverness CT | 4-0 | Buckie Thistle | |||
| r2 | Montrose | 1-0 | Stirling Albion | |||
| r2 | Peterhead | 0-1 | East Fife | |||
| r2 | Cove Rangers | 0-0 | Stenhousemuir | p4-2 | ||
| r2 | Aberdeen U20 | 1-1 | Arbroath | p4-1 | ||
| Southern Section | ||||||
| Tuesday, 31 August 2021 | ||||||
| r2 | Hamilton | 3-2 | Hearts B | |||
| Friday, 3 September 2021 | ||||||
| r2 | Airdrieonians | 1-1 | Queen's Park | p4-5 | ||
| Saturday, 4 September 2021 | ||||||
| r2 | Kilmarnock | 3-1 | Falkirk | |||
| r2 | Stranraer | 0-2 | Partick Thistle | |||
| r2 | Albion Rovers | 6-0 | St.Mirren U20 | |||
| r2 | Celtic B | 1-3 | Morton | |||
| Sunday, 5 September 2021 | ||||||
| r2 | Queen of the South | 3-0 | Broomhill | |||
| Tuesday, 14 September 2021 | ||||||
| r2 | Rangers B | 3-0 | Ayr United | |||
| Score awarded as 3-0. | ||||||
| 4 | +4 | Kyle DOHERTY (Albion Rovers) |
| 2 | +1 | Michael RUTH (Aberdeen U20) |
| +1 | Grant GILLESPIE (Queen's Park) | |
| Kane HESTER (Elgin City) | ||
| +2 | Billy McKAY (Inverness CT) | |
| +2 | Fraser MURRAY (Kilmarnock) | |
| Niah PAYNE (Peterhead) |
