| League Cup | 24.07.18 | Airdrieonians FC | - | Annan Athletic | 4:1 | ||||
| League Cup | 10.10.20 | Annan Athletic | - | Stranraer FC | 4:5 d.p. | ||||
| League Two | 07.08.21 | Stranraer FC | - | Annan Athletic | 0:3 | ||||
| League Two | 17.09.22 | Annan Athletic | - | East Fife FC | 2:2 | ||||
| League Two | 03.12.22 | East Fife FC | - | Annan Athletic | 1:3 | ||||
| League Two | 28.01.23 | Annan Athletic | - | East Fife FC | 3:0 |  |
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| Playoffs | 13.05.25 | East Fife FC | - | Annan Athletic | 3:2 |
Schotland