| 1 | Sat 2 Aug 2014 | 31-5 v Dunfermline AthleticDunfermline Athletic 5-1 Annan Athletic | Scottish Communities Cup First Round |
| 2 | Sat 9 Aug 2014 | 61-2 v Albion RoversAlbion Rovers 2-1 Annan Athletic | Scottish League Two |
| 3 | Sat 16 Aug 2014 | 20-1 v Queens ParkAnnan Athletic 0-1 Queens Park | Scottish League Two |
| 4 | Sat 23 Aug 2014 | 20-2 v MontroseMontrose 2-0 Annan Athletic | Scottish League Two |
| 5 | Sat 30 Aug 2014 | 153-3 v Elgin CityAnnan Athletic 3-3 Elgin City | Scottish League Two |
| 6 | Sat 13 Sep 2014 | 152-0 v Berwick RangersAnnan Athletic 2-0 Berwick Rangers | Scottish League Two |
| 7 | Sat 20 Sep 2014 | 61-0 v East StirlingshireEast Stirlingshire 0-1 Annan Athletic | Scottish League Two |
| 8 | Sat 18 Oct 2014 | 161-1 v East FifeEast Fife 1-1 Annan Athletic | Scottish League Two |
| 9 | Tue 21 Oct 2014 | 60-1 v ArbroathAnnan Athletic 0-1 Arbroath | Scottish League Two |
| 10 | Sat 25 Oct 2014 | 64-3 v East StirlingshireAnnan Athletic 4-3 East Stirlingshire | Scottish League Two |
| 11 | Sat 1 Nov 2014 | 63-2 v LivingstonAnnan Athletic 3-2 Livingston | Scottish FA Cup Third Round |
| 12 | Tue 11 Nov 2014 | 60-0 v Elgin CityElgin City 0-0 Annan Athletic | Scottish League Two |
| 13 | Sat 15 Nov 2014 | 62-2 v MontroseAnnan Athletic 2-2 Montrose | Scottish League Two |
| 14 | Sat 22 Nov 2014 | 60-2 v Berwick RangersBerwick Rangers 2-0 Annan Athletic | Scottish League Two |
| 15 | Sat 29 Nov 2014 | 61-1 v Brechin CityAnnan Athletic 1-1 Brechin City | Scottish FA Cup Fourth Round |
| 16 | Tue 2 Dec 2014 | 62-1 v Albion RoversAnnan Athletic 2-1 Albion Rovers | Scottish League Two |
| 17 | Sat 6 Dec 2014 | 62-3 v ArbroathArbroath 3-2 Annan Athletic | Scottish League Two |
| 18 | Tue 9 Dec 2014 | 62-4 v Brechin CityBrechin City 4-2 Annan Athletic | Scottish FA Cup Fourth Round |
| 19 | Sat 13 Dec 2014 | 62-1 v East FifeAnnan Athletic 2-1 East Fife | Scottish League Two |
| 20 | Sat 28 Feb 2015 | 181-2 v East FifeEast Fife 2-1 Annan Athletic | Scottish League Two |
| 21 | Tue 3 Mar 2015 | 30-1 v ClydeClyde 1-0 Annan Athletic | Scottish League Two |
| 22 | Sat 7 Mar 2015 | 61-3 v Albion RoversAnnan Athletic 1-3 Albion Rovers | Scottish League Two |
| 23 | Sat 14 Mar 2015 | 62-2 v Berwick RangersBerwick Rangers 2-2 Annan Athletic | Scottish League Two |
| 24 | Sat 21 Mar 2015 | 63-2 v East StirlingshireAnnan Athletic 3-2 East Stirlingshire | Scottish League Two |
| 25 | Sat 28 Mar 2015 | 70-1 v ClydeAnnan Athletic 0-1 Clyde | Scottish League Two |
| 26 | Sat 4 Apr 2015 | 61-1 v ArbroathArbroath 1-1 Annan Athletic | Scottish League Two |
| 27 | Sat 11 Apr 2015 | 60-2 v Queens ParkQueens Park 2-0 Annan Athletic | Scottish League Two |
| 28 | Sat 18 Apr 2015 | 62-1 v East FifeAnnan Athletic 2-1 East Fife | Scottish League Two |
| 29 | Sat 25 Apr 2015 | 65-4 v Elgin CityElgin City 4-5 Annan Athletic | Scottish League Two |
| 30 | Sat 2 May 2015 | 64-3 v MontroseAnnan Athletic 4-3 Montrose | Scottish League Two |
Football Web Pages