| 1 | Sat 2 Aug 2014 | 11-5 v Dunfermline AthleticDunfermline Athletic 5-1 Annan Athletic | Scottish Communities Cup First Round |
| 2 | Sat 9 Aug 2014 | 11-2 v Albion RoversAlbion Rovers 2-1 Annan Athletic | Scottish League Two |
| 3 | Sat 16 Aug 2014 | 10-1 v Queens ParkAnnan Athletic 0-1 Queens Park | Scottish League Two |
| 4 | Sat 23 Aug 2014 | 10-2 v MontroseMontrose 2-0 Annan Athletic | Scottish League Two |
| 5 | Sat 30 Aug 2014 | 13-3 v Elgin CityAnnan Athletic 3-3 Elgin City | Scottish League Two |
| 6 | Sat 13 Sep 2014 | 12-0 v Berwick RangersAnnan Athletic 2-0 Berwick Rangers | Scottish League Two |
| 7 | Sat 20 Sep 2014 | 11-0 v East StirlingshireEast Stirlingshire 0-1 Annan Athletic | Scottish League Two |
| 8 | Sat 27 Sep 2014 | 11-1 v ClydeClyde 1-1 Annan Athletic | Scottish League Two |
| 9 | Sat 18 Oct 2014 | 11-1 v East FifeEast Fife 1-1 Annan Athletic | Scottish League Two |
| 10 | Tue 21 Oct 2014 | 10-1 v ArbroathAnnan Athletic 0-1 Arbroath | Scottish League Two |
| 11 | Sat 25 Oct 2014 | 14-3 v East StirlingshireAnnan Athletic 4-3 East Stirlingshire | Scottish League Two |
| 12 | Sat 1 Nov 2014 | 13-2 v LivingstonAnnan Athletic 3-2 Livingston | Scottish FA Cup Third Round |
| 13 | Tue 11 Nov 2014 | 10-0 v Elgin CityElgin City 0-0 Annan Athletic | Scottish League Two |
| 14 | Sat 15 Nov 2014 | 12-2 v MontroseAnnan Athletic 2-2 Montrose | Scottish League Two |
| 15 | Sat 22 Nov 2014 | 10-2 v Berwick RangersBerwick Rangers 2-0 Annan Athletic | Scottish League Two |
| 16 | Sat 29 Nov 2014 | 11-1 v Brechin CityAnnan Athletic 1-1 Brechin City | Scottish FA Cup Fourth Round |
| 17 | Tue 2 Dec 2014 | 12-1 v Albion RoversAnnan Athletic 2-1 Albion Rovers | Scottish League Two |
| 18 | Sat 6 Dec 2014 | 12-3 v ArbroathArbroath 3-2 Annan Athletic | Scottish League Two |
| 19 | Tue 9 Dec 2014 | 12-4 v Brechin CityBrechin City 4-2 Annan Athletic | Scottish FA Cup Fourth Round |
| 20 | Sat 13 Dec 2014 | 12-1 v East FifeAnnan Athletic 2-1 East Fife | Scottish League Two |
| 21 | Sat 20 Dec 2014 | 10-0 v Queens ParkQueens Park 0-0 Annan Athletic | Scottish League Two |
| 22 | Sat 3 Jan 2015 | 10-2 v Albion RoversAlbion Rovers 2-0 Annan Athletic | Scottish League Two |
| 23 | Sat 10 Jan 2015 | 12-3 v Elgin CityAnnan Athletic 2-3 Elgin City | Scottish League Two |
| 24 | Sat 17 Jan 2015 | 13-1 v East StirlingshireEast Stirlingshire 1-3 Annan Athletic | Scottish League Two |
| 25 | Sat 24 Jan 2015 | 14-2 v Berwick RangersAnnan Athletic 4-2 Berwick Rangers | Scottish League Two |
| 26 | Sat 31 Jan 2015 | 11-2 v MontroseMontrose 2-1 Annan Athletic | Scottish League Two |
| 27 | Sat 14 Feb 2015 | 12-0 v Queens ParkAnnan Athletic 2-0 Queens Park | Scottish League Two |
| 28 | Sat 28 Mar 2015 | 10-1 v ClydeAnnan Athletic 0-1 Clyde | Scottish League Two |
| 29 | Sat 4 Apr 2015 | 11-1 v ArbroathArbroath 1-1 Annan Athletic | Scottish League Two |
| 30 | Sat 11 Apr 2015 | 10-2 v Queens ParkQueens Park 2-0 Annan Athletic | Scottish League Two |
| 31 | Sat 2 May 2015 | 14-3 v MontroseAnnan Athletic 4-3 Montrose | Scottish League Two |
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