League Two | 11/12/21 | Annan Athletic | - | Elgin City | 4:1 | ||||
League Cup | 16/07/22 | Annan Athletic | - | Elgin City | 4:0 | ||||
League One | 12/08/23 | Annan Athletic | - | Montrose FC | 1:3 | ||||
League One | 11/11/23 | Montrose FC | - | Annan Athletic | 1:1 | ||||
League One | 16/03/24 | Montrose FC | - | Annan Athletic | 1:1 |