| 1 | Sat 6 Aug 2016 | 103-2 v Stirling AlbionAnnan Athletic 3-2 Stirling Albion | Ladbrokes League Two |
| 2 | Sat 13 Aug 2016 | 100-2 v Berwick RangersBerwick Rangers 2-0 Annan Athletic | Ladbrokes League Two |
| 3 | Sat 20 Aug 2016 | 103-2 v ClydeAnnan Athletic 3-2 Clyde | Ladbrokes League Two |
| 4 | Sat 27 Aug 2016 | 102-2 v MontroseMontrose 2-2 Annan Athletic | Ladbrokes League Two |
| 5 | Sat 10 Sep 2016 | 101-2 v Forfar AthleticAnnan Athletic 1-2 Forfar Athletic | Ladbrokes League Two |
| 6 | Sat 17 Sep 2016 | 101-1 v ArbroathArbroath 1-1 Annan Athletic | Ladbrokes League Two |
| 7 | Sat 24 Sep 2016 | 101-1 v Edinburgh CityAnnan Athletic 1-1 Edinburgh City | Ladbrokes League Two |
| 8 | Sat 15 Oct 2016 | 192-2 v CowdenbeathCowdenbeath 2-2 Annan Athletic | Ladbrokes League Two |
| 9 | Sat 5 Nov 2016 | 71-2 v ArbroathAnnan Athletic 1-2 Arbroath | Ladbrokes League Two |
| 10 | Sat 12 Nov 2016 | 150-1 v Edinburgh CityEdinburgh City 1-0 Annan Athletic | Ladbrokes League Two |
| 11 | Sat 19 Nov 2016 | 101-0 v Elgin CityAnnan Athletic 1-0 Elgin City | Ladbrokes League Two |
| 12 | Sat 10 Dec 2016 | 192-0 v CowdenbeathAnnan Athletic 2-0 Cowdenbeath | Ladbrokes League Two |
| 13 | Tue 13 Dec 2016 | 191-5 v Forfar AthleticForfar Athletic 5-1 Annan Athletic | Ladbrokes League Two |
| 14 | Sat 17 Dec 2016 | 71-3 v Stirling AlbionStirling Albion 3-1 Annan Athletic | Ladbrokes League Two |
| 15 | Sat 24 Dec 2016 | 103-1 v Berwick RangersAnnan Athletic 3-1 Berwick Rangers | Ladbrokes League Two |
| 16 | Sat 31 Dec 2016 | 103-2 v ClydeClyde 2-3 Annan Athletic | Ladbrokes League Two |
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