| 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 | Sat 10 Aug 2013 | 2-2 v PeterheadPeterhead 2-2 Annan Athletic | Scottish League Two |
| 4 | Sat 17 Aug 2013 | 22-1 v MontroseAnnan Athletic 2-1 Montrose | Scottish League Two |
| 5 | Tue 20 Aug 2013 | 23-2 v StranraerStranraer 2-3 Annan Athletic | Ramsdens Cup Quarter Final |
| 6 | Sat 24 Aug 2013 | 21-1 v Albion RoversAnnan Athletic 1-1 Albion Rovers | Scottish League Two |
| 7 | Sat 31 Aug 2013 | 22-4 v Berwick RangersBerwick Rangers 4-2 Annan Athletic | Scottish League Two |
| 8 | Sat 7 Sep 2013 | 24-0 v Formartine UnitedAnnan Athletic 4-0 Formartine United | Ramsdens Cup Semi Final |
| 9 | Sat 14 Sep 2013 | 22-0 v Stirling AlbionStirling Albion 0-2 Annan Athletic | Scottish League Two |
| 10 | Sat 21 Sep 2013 | 21-2 v ClydeAnnan Athletic 1-2 Clyde | Scottish League Two |
| 11 | Sat 28 Sep 2013 | 25-2 v Queens ParkQueens Park 2-5 Annan Athletic | Scottish League Two |
| 12 | Sat 5 Oct 2013 | 20-0 v Buckie ThistleBuckie Thistle 0-0 Annan Athletic | Scottish FA Cup Second Round |
| 13 | Sun 13 Oct 2013 | 20-3 v Raith RoversRaith Rovers 3-0 Annan Athletic | Ramsdens Cup Semi Final |
| 14 | Sat 19 Oct 2013 | 24-0 v Buckie ThistleAnnan Athletic 4-0 Buckie Thistle | Scottish FA Cup Second Round |
| 15 | Sat 26 Oct 2013 | 23-2 v Elgin CityElgin City 2-3 Annan Athletic | Scottish League Two |
| 16 | Sat 22 Feb 2014 | 161-0 v Queens ParkQueens Park 0-1 Annan Athletic | Scottish League Two |
| 17 | Tue 25 Feb 2014 | 73-2 v Queens ParkAnnan Athletic 3-2 Queens Park | Scottish League Two |
| 18 | Sat 1 Mar 2014 | 74-0 v Berwick RangersAnnan Athletic 4-0 Berwick Rangers | Scottish League Two |
| 19 | Tue 4 Mar 2014 | 71-3 v PeterheadPeterhead 3-1 Annan Athletic | Scottish League Two |
| 20 | Sat 15 Mar 2014 | 23-2 v Elgin CityElgin City 2-3 Annan Athletic | Scottish League Two |
| 21 | Sat 22 Mar 2014 | 22-1 v PeterheadAnnan Athletic 2-1 Peterhead | Scottish League Two |
| 22 | Tue 25 Mar 2014 | 22-0 v Albion RoversAlbion Rovers 0-2 Annan Athletic | Scottish League Two |
| 23 | Sat 29 Mar 2014 | 21-2 v Stirling AlbionAnnan Athletic 1-2 Stirling Albion | Scottish League Two |
| 24 | Sat 5 Apr 2014 | 23-0 v ClydeClyde 0-3 Annan Athletic | Scottish League Two |
| 25 | Sat 12 Apr 2014 | 21-2 v East StirlingshireEast Stirlingshire 2-1 Annan Athletic | Scottish League Two |
| 26 | Sat 19 Apr 2014 | 21-1 v Queens ParkAnnan Athletic 1-1 Queens Park | Scottish League Two |
| 27 | Sat 26 Apr 2014 | 21-2 v MontroseMontrose 2-1 Annan Athletic | Scottish League Two |
| 28 | Sat 3 May 2014 | 22-0 v Elgin CityAnnan Athletic 2-0 Elgin City | Scottish League Two |
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