Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 23.03.2021 |  | 2. Round | Elgin City - Ayr United | Elg - | 0:4 | Unter Ausschluss der Öffentlichkeit. |
| 08.05.2021 |  | Semi-finals First leg | Elgin City - Edinburgh City | Elg - EC | 0:1 | |
| 10.07.2021 |  | Group B | Elgin City - Arbroath FC | Elg - Arb | 0:1 | 220 |
| 20.07.2021 | | Group B | Elgin City - Kelty Hearts | Elg - KH | 1:3 | 220 |
| 31.07.2021 |  | Matchday 1 | Elgin City - Stranraer FC | Elg - Str | 1:1 | 405 |
| 14.08.2021 | | Matchday 3 | Elgin City - Albion Rovers | Elg - ALB | 3:0 | 488 |
| 21.08.2021 | | Matchday 4 | Elgin City - Forfar Athletic | Elg - FOR | 1:1 | 633 |
| 18.09.2021 | | Matchday 7 | Elgin City - Annan Athletic | Elg - | 0:2 | 467 |
| 02.10.2021 | | Matchday 9 | Elgin City - Stirling Albion | Elg - Sti | 0:2 | 652 |
| 13.11.2021 | | Matchday 13 | Elgin City - Cowdenbeath FC | Elg - | 1:0 | 650 |
| 23.11.2021 | | Matchday 11 | Elgin City - Edinburgh City | Elg - EC | 1:1 | 378 |
| 18.12.2021 | | Matchday 17 | Elgin City - Stenhousemuir | Elg - Ste | 2:2 | 518 |