| 1 | Sat 27 Jul 2013 | 1-0 v MortonAnnan Athletic 1-0 Morton | Ramsdens Cup Second Round |
| 2 | Sat 3 Aug 2013 | 160-3 v Queen of the SouthQueen of the South 3-0 Annan Athletic | Scottish Communities Cup First Round |
| 3 | Sat 24 Aug 2013 | 161-1 v Albion RoversAnnan Athletic 1-1 Albion Rovers | Scottish League Two |
| 4 | Sat 31 Aug 2013 | 162-4 v Berwick RangersBerwick Rangers 4-2 Annan Athletic | Scottish League Two |
| 5 | Sat 7 Sep 2013 | 164-0 v Formartine UnitedAnnan Athletic 4-0 Formartine United | Ramsdens Cup Semi Final |
| 6 | Sun 13 Oct 2013 | 150-3 v Raith RoversRaith Rovers 3-0 Annan Athletic | Ramsdens Cup Semi Final |
| 7 | Sat 28 Dec 2013 | 162-1 v Elgin CityAnnan Athletic 2-1 Elgin City | Scottish League Two |
| 8 | Sat 4 Jan 2014 | 162-0 v Albion RoversAnnan Athletic 2-0 Albion Rovers | Scottish League Two |
| 9 | Sat 11 Jan 2014 | 164-1 v Berwick RangersBerwick Rangers 1-4 Annan Athletic | Scottish League Two |
| 10 | Sat 25 Jan 2014 | 161-1 v Stirling AlbionStirling Albion 1-1 Annan Athletic | Scottish League Two |
| 11 | Sat 15 Feb 2014 | 162-3 v East StirlingshireAnnan Athletic 2-3 East Stirlingshire | Scottish League Two |
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