Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 09.01.2021 |  | 2. Round | East Fife - Tranent | Eas - | 5:1 | Unter Ausschluss der Öffentlichkeit. |
| 03.04.2021 | | 3. Round | East Fife - Morton | Eas - Mor | 1:2 | Unter Ausschluss der Öffentlichkeit. |
| 20.07.2021 |  | Group B | East Fife - Dundee Utd | Eas - DUN | 0:1 | 362 |
| 24.07.2021 | | Group B | East Fife - Elgin City | Eas - Elg | 2:3 | 100 |
| 31.07.2021 |  | Matchday 1 | East Fife - Queen's Park FC | Eas - | 1:1 | 320 |
| 21.08.2021 | | Matchday 4 | East Fife - Montrose FC | Eas - Mon | 0:2 | 488 |
| 28.08.2021 | | Matchday 5 | East Fife - Peterhead | Eas - Pet | 3:0 | 373 |
| 25.09.2021 | | Matchday 8 | East Fife - Clyde FC | Eas - | 0:2 | 481 |
| 16.10.2021 | | Matchday 10 | East Fife - Cove Rangers | Eas - | 4:2 | 409 |
| 30.10.2021 | | Matchday 12 | East Fife - Dumbarton FC | Eas - DUM | 2:1 | 442 |
| 13.11.2021 | | Matchday 14 | East Fife - Airdrieonians | Eas - AIR | 0:1 | 651 |
| 04.12.2021 | | Matchday 16 | East Fife - Alloa Ath. | Eas - ALL | 1:1 | 427 |