| 1 | Tue 17 Jul 2018 | 4-0 v Berwick RangersAnnan Athletic 4-0 Berwick Rangers | Betfred Cup Group F |
| 2 | Sat 21 Jul 2018 | 0-1 v LivingstonLivingston 1-0 Annan Athletic | Betfred Cup Group F |
| 3 | Tue 24 Jul 2018 | 1-4 v AirdrieoniansAirdrieonians 4-1 Annan Athletic | Betfred Cup Group F |
| 4 | Sat 8 Sep 2018 | 0-3 v ArbroathArbroath 3-0 Annan Athletic | IRN-BRU Cup Second Round |
| 5 | Sat 24 Nov 2018 | 0-0 v MontroseMontrose 0-0 Annan Athletic | William Hill Scottish Cup Third Round |
| 6 | Tue 27 Nov 2018 | 3-4 v MontroseAnnan Athletic 3-4 Montrose | William Hill Scottish Cup Third Round Replay |
| 7 | Sat 22 Dec 2018 | 4-0 v Berwick RangersAnnan Athletic 4-0 Berwick Rangers | Ladbrokes League Two |
| 8 | Sat 29 Dec 2018 | 1-1 v Albion RoversAlbion Rovers 1-1 Annan Athletic | Ladbrokes League Two |
| 9 | Sat 5 Jan 2019 | 2-0 v Elgin CityAnnan Athletic 2-0 Elgin City | Ladbrokes League Two |
| 10 | Sat 12 Jan 2019 | 1-2 v Stirling AlbionStirling Albion 2-1 Annan Athletic | Ladbrokes League Two |
| 11 | Sat 19 Jan 2019 | 2-1 v Edinburgh CityEdinburgh City 1-2 Annan Athletic | Ladbrokes League Two |
| 12 | Sat 20 Apr 2019 | 3-0 v Queens ParkQueens Park 0-3 Annan Athletic | Ladbrokes League Two |
| 13 | Sat 27 Apr 2019 | 3-2 v CowdenbeathAnnan Athletic 3-2 Cowdenbeath | Ladbrokes League Two |
| 14 | Sat 4 May 2019 | 2-0 v Albion RoversAlbion Rovers 0-2 Annan Athletic | Ladbrokes League Two |
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