| 1 | Sat 10 Aug 2013 | 42-2 v PeterheadPeterhead 2-2 Annan Athletic | Scottish League Two |
| 2 | Sat 17 Aug 2013 | 42-1 v MontroseAnnan Athletic 2-1 Montrose | Scottish League Two |
| 3 | Tue 20 Aug 2013 | 43-2 v StranraerStranraer 2-3 Annan Athletic | Ramsdens Cup Quarter Final |
| 4 | Sat 24 Aug 2013 | 41-1 v Albion RoversAnnan Athletic 1-1 Albion Rovers | Scottish League Two |
| 5 | Sat 31 Aug 2013 | 42-4 v Berwick RangersBerwick Rangers 4-2 Annan Athletic | Scottish League Two |
| 6 | Sun 13 Oct 2013 | 60-3 v Raith RoversRaith Rovers 3-0 Annan Athletic | Ramsdens Cup Semi Final |
| 7 | Sat 19 Oct 2013 | 124-0 v Buckie ThistleAnnan Athletic 4-0 Buckie Thistle | Scottish FA Cup Second Round |
| 8 | Tue 12 Nov 2013 | 122-4 v StenhousemuirAnnan Athletic 2-4 Stenhousemuir | Scottish FA Cup Third Round |
| 9 | Tue 3 Dec 2013 | 81-2 v ClydeClyde 2-1 Annan Athletic | Scottish League Two |
| 10 | Sat 7 Dec 2013 | 81-1 v East StirlingshireEast Stirlingshire 1-1 Annan Athletic | Scottish League Two |
| 11 | Sat 8 Feb 2014 | 41-0 v MontroseAnnan Athletic 1-0 Montrose | Scottish League Two |
| 12 | Sat 15 Feb 2014 | 42-3 v East StirlingshireAnnan Athletic 2-3 East Stirlingshire | Scottish League Two |
| 13 | Tue 25 Feb 2014 | 123-2 v Queens ParkAnnan Athletic 3-2 Queens Park | Scottish League Two |
| 14 | Sat 1 Mar 2014 | 54-0 v Berwick RangersAnnan Athletic 4-0 Berwick Rangers | Scottish League Two |
| 15 | Tue 4 Mar 2014 | 51-3 v PeterheadPeterhead 3-1 Annan Athletic | Scottish League Two |
| 16 | Sat 15 Mar 2014 | 63-2 v Elgin CityElgin City 2-3 Annan Athletic | Scottish League Two |
| 17 | Sat 22 Mar 2014 | 62-1 v PeterheadAnnan Athletic 2-1 Peterhead | Scottish League Two |
| 18 | Tue 25 Mar 2014 | 62-0 v Albion RoversAlbion Rovers 0-2 Annan Athletic | Scottish League Two |
| 19 | Sat 29 Mar 2014 | 61-2 v Stirling AlbionAnnan Athletic 1-2 Stirling Albion | Scottish League Two |
| 20 | Sat 3 May 2014 | 72-0 v Elgin CityAnnan Athletic 2-0 Elgin City | Scottish League Two |
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