| 1 | Sat 6 Aug 2016 | 33-2 v Stirling AlbionAnnan Athletic 3-2 Stirling Albion | Ladbrokes League Two |
| 2 | Sat 13 Aug 2016 | 30-2 v Berwick RangersBerwick Rangers 2-0 Annan Athletic | Ladbrokes League Two |
| 3 | Sat 20 Aug 2016 | 33-2 v ClydeAnnan Athletic 3-2 Clyde | Ladbrokes League Two |
| 4 | Sat 27 Aug 2016 | 32-2 v MontroseMontrose 2-2 Annan Athletic | Ladbrokes League Two |
| 5 | Sat 10 Sep 2016 | 31-2 v Forfar AthleticAnnan Athletic 1-2 Forfar Athletic | Ladbrokes League Two |
| 6 | Sat 15 Oct 2016 | 182-2 v CowdenbeathCowdenbeath 2-2 Annan Athletic | Ladbrokes League Two |
| 7 | Sat 5 Nov 2016 | 21-2 v ArbroathAnnan Athletic 1-2 Arbroath | Ladbrokes League Two |
| 8 | Sat 12 Nov 2016 | 20-1 v Edinburgh CityEdinburgh City 1-0 Annan Athletic | Ladbrokes League Two |
| 9 | Sat 19 Nov 2016 | 21-0 v Elgin CityAnnan Athletic 1-0 Elgin City | Ladbrokes League Two |
| 10 | Sat 10 Dec 2016 | 22-0 v CowdenbeathAnnan Athletic 2-0 Cowdenbeath | Ladbrokes League Two |
| 11 | Tue 13 Dec 2016 | 21-5 v Forfar AthleticForfar Athletic 5-1 Annan Athletic | Ladbrokes League Two |
| 12 | Sat 17 Dec 2016 | 21-3 v Stirling AlbionStirling Albion 3-1 Annan Athletic | Ladbrokes League Two |
| 13 | Sat 24 Dec 2016 | 33-1 v Berwick RangersAnnan Athletic 3-1 Berwick Rangers | Ladbrokes League Two |
| 14 | Sat 31 Dec 2016 | 33-2 v ClydeClyde 2-3 Annan Athletic | Ladbrokes League Two |
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