| 1 | Sat 2 Aug 2014 | 61-5 v Dunfermline AthleticDunfermline Athletic 5-1 Annan Athletic | Scottish Communities Cup First Round |
| 2 | Sat 9 Aug 2014 | 51-2 v Albion RoversAlbion Rovers 2-1 Annan Athletic | Scottish League Two |
| 3 | Sat 16 Aug 2014 | 60-1 v Queens ParkAnnan Athletic 0-1 Queens Park | Scottish League Two |
| 4 | Tue 21 Oct 2014 | 170-1 v ArbroathAnnan Athletic 0-1 Arbroath | Scottish League Two |
| 5 | Sat 6 Dec 2014 | 172-3 v ArbroathArbroath 3-2 Annan Athletic | Scottish League Two |
| 6 | Tue 9 Dec 2014 | 72-4 v Brechin CityBrechin City 4-2 Annan Athletic | Scottish FA Cup Fourth Round |
| 7 | Sat 13 Dec 2014 | 32-1 v East FifeAnnan Athletic 2-1 East Fife | Scottish League Two |
| 8 | Sat 17 Jan 2015 | 33-1 v East StirlingshireEast Stirlingshire 1-3 Annan Athletic | Scottish League Two |
| 9 | Sat 24 Jan 2015 | 34-2 v Berwick RangersAnnan Athletic 4-2 Berwick Rangers | Scottish League Two |
| 10 | Sat 31 Jan 2015 | 31-2 v MontroseMontrose 2-1 Annan Athletic | Scottish League Two |
| 11 | Sat 14 Feb 2015 | 32-0 v Queens ParkAnnan Athletic 2-0 Queens Park | Scottish League Two |
| 12 | Sat 21 Feb 2015 | 32-0 v ArbroathAnnan Athletic 2-0 Arbroath | Scottish League Two |
| 13 | Sat 28 Feb 2015 | 31-2 v East FifeEast Fife 2-1 Annan Athletic | Scottish League Two |
| 14 | Sat 14 Mar 2015 | 52-2 v Berwick RangersBerwick Rangers 2-2 Annan Athletic | Scottish League Two |
| 15 | Sat 21 Mar 2015 | 33-2 v East StirlingshireAnnan Athletic 3-2 East Stirlingshire | Scottish League Two |
| 16 | Sat 28 Mar 2015 | 30-1 v ClydeAnnan Athletic 0-1 Clyde | Scottish League Two |
| 17 | Sat 4 Apr 2015 | 31-1 v ArbroathArbroath 1-1 Annan Athletic | Scottish League Two |
| 18 | Sat 11 Apr 2015 | 30-2 v Queens ParkQueens Park 2-0 Annan Athletic | Scottish League Two |
| 19 | Sat 18 Apr 2015 | 32-1 v East FifeAnnan Athletic 2-1 East Fife | Scottish League Two |
| 20 | Sat 25 Apr 2015 | 35-4 v Elgin CityElgin City 4-5 Annan Athletic | Scottish League Two |
| 21 | Sat 2 May 2015 | 34-3 v MontroseAnnan Athletic 4-3 Montrose | Scottish League Two |
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