| 1 | Sat 27 Jul 2013 | 1-0 v MortonAnnan Athletic 1-0 Morton | Ramsdens Cup Second Round |
| 2 | Sat 3 Aug 2013 | 0-3 v Queen of the SouthQueen of the South 3-0 Annan Athletic | Scottish Communities Cup First Round |
| 3 | Tue 20 Aug 2013 | 153-2 v StranraerStranraer 2-3 Annan Athletic | Ramsdens Cup Quarter Final |
| 4 | Sat 28 Sep 2013 | 185-2 v Queens ParkQueens Park 2-5 Annan Athletic | Scottish League Two |
| 5 | Sun 13 Oct 2013 | 30-3 v Raith RoversRaith Rovers 3-0 Annan Athletic | Ramsdens Cup Semi Final |
| 6 | Sat 2 Nov 2013 | 62-2 v StenhousemuirStenhousemuir 2-2 Annan Athletic | Scottish FA Cup Third Round |
| 7 | Tue 5 Nov 2013 | 62-0 v PeterheadAnnan Athletic 2-0 Peterhead | Scottish League Two |
| 8 | Sat 9 Nov 2013 | 60-2 v Albion RoversAlbion Rovers 2-0 Annan Athletic | Scottish League Two |
| 9 | Tue 12 Nov 2013 | 62-4 v StenhousemuirAnnan Athletic 2-4 Stenhousemuir | Scottish FA Cup Third Round |
| 10 | Sat 16 Nov 2013 | 63-2 v Berwick RangersAnnan Athletic 3-2 Berwick Rangers | Scottish League Two |
| 11 | Sat 23 Nov 2013 | 64-4 v Stirling AlbionAnnan Athletic 4-4 Stirling Albion | Scottish League Two |
| 12 | Tue 3 Dec 2013 | 61-2 v ClydeClyde 2-1 Annan Athletic | Scottish League Two |
| 13 | Sat 7 Dec 2013 | 61-1 v East StirlingshireEast Stirlingshire 1-1 Annan Athletic | Scottish League Two |
| 14 | Sat 28 Dec 2013 | 52-1 v Elgin CityAnnan Athletic 2-1 Elgin City | Scottish League Two |
| 15 | Sat 4 Jan 2014 | 52-0 v Albion RoversAnnan Athletic 2-0 Albion Rovers | Scottish League Two |
| 16 | Sat 11 Jan 2014 | 54-1 v Berwick RangersBerwick Rangers 1-4 Annan Athletic | Scottish League Two |
| 17 | Sat 25 Jan 2014 | 51-1 v Stirling AlbionStirling Albion 1-1 Annan Athletic | Scottish League Two |
| 18 | Sat 8 Feb 2014 | 51-0 v MontroseAnnan Athletic 1-0 Montrose | Scottish League Two |
| 19 | Sat 15 Feb 2014 | 52-3 v East StirlingshireAnnan Athletic 2-3 East Stirlingshire | Scottish League Two |
| 20 | Sat 22 Feb 2014 | 51-0 v Queens ParkQueens Park 0-1 Annan Athletic | Scottish League Two |
| 21 | Tue 25 Feb 2014 | 53-2 v Queens ParkAnnan Athletic 3-2 Queens Park | Scottish League Two |
| 22 | Sat 15 Mar 2014 | 53-2 v Elgin CityElgin City 2-3 Annan Athletic | Scottish League Two |
| 23 | Sat 22 Mar 2014 | 52-1 v PeterheadAnnan Athletic 2-1 Peterhead | Scottish League Two |
| 24 | Tue 25 Mar 2014 | 52-0 v Albion RoversAlbion Rovers 0-2 Annan Athletic | Scottish League Two |
| 25 | Sat 29 Mar 2014 | 51-2 v Stirling AlbionAnnan Athletic 1-2 Stirling Albion | Scottish League Two |
| 26 | Sat 5 Apr 2014 | 53-0 v ClydeClyde 0-3 Annan Athletic | Scottish League Two |
| 27 | Sat 12 Apr 2014 | 51-2 v East StirlingshireEast Stirlingshire 2-1 Annan Athletic | Scottish League Two |
| 28 | Sat 19 Apr 2014 | 51-1 v Queens ParkAnnan Athletic 1-1 Queens Park | Scottish League Two |
| 29 | Sat 26 Apr 2014 | 51-2 v MontroseMontrose 2-1 Annan Athletic | Scottish League Two |
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