| 1 | Sat 23 Sep 2017 | 2-3 v Stirling AlbionStirling Albion 3-2 Annan Athletic | Ladbrokes League Two |
| 2 | Sat 30 Sep 2017 | 1-0 v CowdenbeathAnnan Athletic 1-0 Cowdenbeath | Ladbrokes League Two |
| 3 | Sat 21 Oct 2017 | 1-0 v Edinburgh CityEdinburgh City 0-1 Annan Athletic | Ladbrokes League Two |
| 4 | Sat 28 Oct 2017 | 0-1 v PeterheadPeterhead 1-0 Annan Athletic | Ladbrokes League Two |
| 5 | Sat 4 Nov 2017 | 0-0 v Berwick RangersAnnan Athletic 0-0 Berwick Rangers | Ladbrokes League Two |
| 6 | Sat 11 Nov 2017 | 1-1 v MontroseMontrose 1-1 Annan Athletic | Ladbrokes League Two |
| 7 | Sat 18 Nov 2017 | 1-1 v CowdenbeathCowdenbeath 1-1 Annan Athletic | Ladbrokes League Two |
| 8 | Sat 10 Feb 2018 | 1-2 v Elgin CityElgin City 2-1 Annan Athletic | Ladbrokes League Two |
| 9 | Sat 17 Feb 2018 | 0-3 v Stirling AlbionStirling Albion 3-0 Annan Athletic | Ladbrokes League Two |
| 10 | Tue 20 Feb 2018 | 3-3 v PeterheadAnnan Athletic 3-3 Peterhead | Ladbrokes League Two |
| 11 | Sat 24 Feb 2018 | 2-0 v StenhousemuirAnnan Athletic 2-0 Stenhousemuir | Ladbrokes League Two |
| 12 | Sat 10 Mar 2018 | 2-3 v Edinburgh CityAnnan Athletic 2-3 Edinburgh City | Ladbrokes League Two |
| 13 | Tue 13 Mar 2018 | 1-2 v MontroseMontrose 2-1 Annan Athletic | Ladbrokes League Two |
| 14 | Sat 17 Mar 2018 | 1-1 v ClydeAnnan Athletic 1-1 Clyde | Ladbrokes League Two |
| 15 | Sat 31 Mar 2018 | 0-0 v Berwick RangersAnnan Athletic 0-0 Berwick Rangers | Ladbrokes League Two |
| 16 | Sat 7 Apr 2018 | 4-1 v Elgin CityAnnan Athletic 4-1 Elgin City | Ladbrokes League Two |
| 17 | Sat 14 Apr 2018 | 2-3 v StenhousemuirStenhousemuir 3-2 Annan Athletic | Ladbrokes League Two |
| 18 | Sat 21 Apr 2018 | 3-1 v Stirling AlbionAnnan Athletic 3-1 Stirling Albion | Ladbrokes League Two |
| 19 | Sat 28 Apr 2018 | 2-0 v CowdenbeathCowdenbeath 0-2 Annan Athletic | Ladbrokes League Two |
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