Challenge Cup| ROUND | R1 | R2 | R3 | QF | SF | F | ||
| N | S | N | S | |||||
| Season archive |
| Northern Section | ||||||
| Tuesday, 10 August 2021 | ||||||
| r1 | East Fife | 1-0 | St.Johnstone U20 | |||
| r1 | Stenhousemuir | 3-0 | Dundee United U20 | |||
| r1 | Forfar Athletic | 1-0 | Formartine United | |||
| r1 | Fraserburgh | 0-1 | Cowdenbeath | |||
| r1 | Brora Rangers | 0-1 | Aberdeen U20 | |||
| r1 | Hibernian U20 | 1-2 | Elgin City | |||
| Wednesday, 11 August 2021 | ||||||
| r1 | Brechin City | 1-3 | Buckie Thistle | |||
| r1 | Dundee B | 1-2 | Peterhead | |||
| Southern Section | ||||||
| Tuesday, 10 August 2021 | ||||||
| r1 | Queen's Park | 1-1 | Bonnyrigg Rose | p5-4 | ||
| r1 | St.Mirren U20 | 1-1 | Kelty Hearts | p3-0 | ||
| Wednesday, 11 August 2021 | ||||||
| r1 | Falkirk | 3-0 | East Kilbride | |||
| r1 | Dumbarton | 2-3 | Rangers B | |||
| r1 | Celtic B | 2-0 | Annan Athletic | |||
| r1 | Broomhill | 1-0 | Clyde | |||
| Tuesday, 17 August 2021 | ||||||
| r1 | Edinburgh City | 0-1 | Hearts B | |||
| Northern Section | |||||
| r1 | Ross County U20 | 0-3 | Stirling Albion | ||
| Southern Section | |||||
| r1 | Livingston U20 | 0-3 | Albion Rovers | ||
| r1 | Stranraer | 3-0 | Motherwell U20 | ||
| 2 | +2 | Kane HESTER (Elgin City) |
| +2 | Niah PAYNE () | |
| 1 | +1 | Euan HENDERSON (, 1p) |
| +1 | Lee O'CONNOR () | |
| +1 | Aidan KEENA () | |
| +1 | Callum MURRAY () | |
| +1 | Sam URQUHART () | |
| +1 | Tony WESTON () | |
| +1 | Scott ROBERTSON () | |
| +1 | Grant GILLESPIE (Queen's Park, 1p) | |
| +1 | Eoghan STOKES () | |
| +1 | Michael TIDSER (Kelty Hearts) | |
| +1 | Matty AITKEN (Forfar Athletic) | |
| +1 | Liam BUCHANAN (Cowdenbeath) | |
| +1 | Nicky JAMIESON (Stenhousemuir) | |
| +1 | Luc BOLLAN () | |
| +1 | Ryan TIERNEY (Stenhousemuir) | |
| +1 | Dean HOSKINS (Bonnyrigg Rose) | |
| +1 | Alex LOWRY () | |
| +1 | Scott MERCER (East Fife) | |
| +1 | Jake HASTIE () | |
| +1 | Michael RUTH (Aberdeen U20) | |
| +1 | Josh JACK (St.Mirren U20) | |
| +1 | Gregor BUCHANAN () | |
| +1 | Corey PANTER () | |
| +1 | Cammy GRAHAM (Stenhousemuir) | |
| +1 | Seb ROSS () |
