| Date | League | Pos | Result | Pos | | xScore | Perf | Home | Away | Wins | Draws | Losses | Points | Pts/Game |
|---|
| 10 Oct | S League 2 | 9 | Annan Athletic 1 - 6 Stranraer | 1 |  | - |  | | | 0/1 | 0/1 | 1/1 | 0/3 | 0.0 |
| 3 Oct | S League 2 | 7 | Annan Athletic 0 - 1 Stirling Albion | 10 | | 2 - 1  |  | | | 0/2 | 0/2 | 2/2 | 0/6 | 0.0 |
| 19 Sep | S League 2 | 8 | Forfar Athletic 1 - 0 Annan Athletic | 6 | | 1 - 0  | | | | 0/3 | 0/3 | 3/3 | 0/9 | 0.0 |
| 12 Sep | S League 2 | 8 | Annan Athletic 2 - 0 Elgin City | 2 |  | 2 - 1  |  | | | 1/4 | 0/4 | 3/4 | 3/12 | 0.8 |
| 5 Sep | S League 2 | 8 | Kelty Hearts 2 - 1 Annan Athletic | 7 | | 1 - 0  | | | | 1/5 | 0/5 | 4/5 | 3/15 | 0.6 |
| 29 Aug | S League 2 | 9 | Annan Athletic 2 - 0 Dumbarton | 10 | | 2 - 1 | | | | 2/6 | 0/6 | 4/6 | 6/18 | 1.0 |
| 22 Aug | S League 2 | 5 | FC Edinburgh 1 - 0 Annan Athletic | 7 | | 0 - 0 | | | | 2/7 | 0/7 | 5/7 | 6/21 | 0.9 |
| 15 Aug | S League 2 | 7 | Annan Athletic 1 - 2 Clyde | 5 | | 2 - 1 | | | | 2/8 | 0/8 | 6/8 | 6/24 | 0.8 |
| 8 Aug | S League 2 | 10 | Stranraer 0 - 1 Annan Athletic | 1 | | - | | | | 3/9 | 0/9 | 6/9 | 9/27 | 1.0 |
| 1 Aug | S League 2 | - | Annan Athletic 2 - 4 Spartans | - | | - | - | | | 3/10 | 0/10 | 7/10 | 9/30 | 0.9 |