| League Cup | 16/07/16 | Annan Athletic | - | Stranraer FC | 1:2 | ||||
| League Cup | 15/07/17 | Clyde FC | - | Annan Athletic | 2:1 | ||||
| League Cup | 16/07/24 | Annan Athletic | - | Bonnyrigg Rose Athletic | 7:6 pso |  |
| League Cup | 16/07/16 | Annan Athletic | - | Stranraer FC | 1:2 | ||||
| League Cup | 15/07/17 | Clyde FC | - | Annan Athletic | 2:1 | ||||
| League Cup | 16/07/24 | Annan Athletic | - | Bonnyrigg Rose Athletic | 7:6 pso | |
| Smart Samuel Osadolor | |
| Born: | 26.03.1991 |
| Place of birth: |
Benin City, 
Nigeria |
| Nationality: |
Nigeria
|
| Height: | 188 cm |
| Weight: | 76 kg |
| Position(s): | Left Winger Left Midfielder |
| Foot: | left |