| League Two | 22.12.21 | Cowdenbeath FC | - | Edinburgh City FC | 1:2 | ||||
| League Two | 19.03.22 | Cowdenbeath FC | - | Stenhousemuir FC | 1:1 | ||||
| League Two | 20.08.22 | East Fife FC | - | Forfar Athletic | 1:0 | ||||
| League Two | 17.09.22 | Annan Athletic | - | East Fife FC | 2:2 |  |
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| League Two | 07.01.23 | Elgin City | - | East Fife FC | 1:2 | |
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| League Two | 25.02.23 | Stranraer FC | - | East Fife FC | 2:0 | ||||
| Playoffs | 09.05.23 | East Fife FC | - | Clyde FC | 0:1 |
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