| League Cup | 24/07/18 | Airdrieonians FC | - | Annan Athletic | 4:1 | ||||
| League Cup | 10/10/20 | Annan Athletic | - | Stranraer FC | 4:5 pso | ||||
| 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 | ||||
| Playoffs | 16/05/25 | Annan Athletic | - | East Fife FC | 1:1 |
Scotland