| League Cup | 13/10/20 | Ayr United | - | Annan Athletic | 1:0 | ||||
| League Cup | 18/07/23 | Dunfermline Athletic | - | Annan Athletic | 4:0 |
| League Cup | 13/10/20 | Ayr United | - | Annan Athletic | 1:0 | ||||
| League Cup | 18/07/23 | Dunfermline Athletic | - | Annan Athletic | 4:0 |
| Joseph Chalmers | |
| Born: | 03.01.1994 |
| Place of birth: |
Cambuslang, 
Scotland |
| Nationality: |
Scotland
|
| Height: | 188 cm |
| Weight: | 80 kg |
| Position(s): | Central Midfielder Left Back |
| Foot: | left |