| 1 | Tue 24 Jul 2018 | 1-4 v AirdrieoniansAirdrieonians 4-1 Annan Athletic | Betfred Cup Group F |
| 2 | Tue 27 Nov 2018 | 3-4 v MontroseAnnan Athletic 3-4 Montrose | William Hill Scottish Cup Third Round Replay |
| 3 | Sat 22 Dec 2018 | 4-0 v Berwick RangersAnnan Athletic 4-0 Berwick Rangers | Ladbrokes League Two |
| 4 | Sat 29 Dec 2018 | 1-1 v Albion RoversAlbion Rovers 1-1 Annan Athletic | Ladbrokes League Two |
| 5 | Sat 5 Jan 2019 | 2-0 v Elgin CityAnnan Athletic 2-0 Elgin City | Ladbrokes League Two |
| 6 | Sat 12 Jan 2019 | 1-2 v Stirling AlbionStirling Albion 2-1 Annan Athletic | Ladbrokes League Two |
| 7 | Sat 19 Jan 2019 | 2-1 v Edinburgh CityEdinburgh City 1-2 Annan Athletic | Ladbrokes League Two |
| 8 | Sat 26 Jan 2019 | 3-0 v PeterheadAnnan Athletic 3-0 Peterhead | Ladbrokes League Two |
| 9 | Sat 9 Feb 2019 | 1-1 v ClydeAnnan Athletic 1-1 Clyde | Ladbrokes League Two |
| 10 | Sat 16 Feb 2019 | 4-2 v CowdenbeathCowdenbeath 2-4 Annan Athletic | Ladbrokes League Two |
| 11 | Sat 23 Feb 2019 | 4-0 v Albion RoversAnnan Athletic 4-0 Albion Rovers | Ladbrokes League Two |
| 12 | Tue 26 Feb 2019 | 2-1 v Berwick RangersBerwick Rangers 1-2 Annan Athletic | Ladbrokes League Two |
| 13 | Sat 2 Mar 2019 | 2-1 v Queens ParkAnnan Athletic 2-1 Queens Park | Ladbrokes League Two |
| 14 | Sat 9 Mar 2019 | 1-2 v PeterheadPeterhead 2-1 Annan Athletic | Ladbrokes League Two |
| 15 | Sat 16 Mar 2019 | 3-1 v Edinburgh CityAnnan Athletic 3-1 Edinburgh City | Ladbrokes League Two |
| 16 | Sat 23 Mar 2019 | 1-2 v ClydeClyde 2-1 Annan Athletic | Ladbrokes League Two |
| 17 | Sat 30 Mar 2019 | 1-0 v Elgin CityElgin City 0-1 Annan Athletic | Ladbrokes League Two |
| 18 | Sat 6 Apr 2019 | 6-0 v Berwick RangersAnnan Athletic 6-0 Berwick Rangers | Ladbrokes League Two |
| 19 | Sat 13 Apr 2019 | 2-2 v Stirling AlbionAnnan Athletic 2-2 Stirling Albion | Ladbrokes League Two |
| 20 | Sat 20 Apr 2019 | 3-0 v Queens ParkQueens Park 0-3 Annan Athletic | Ladbrokes League Two |
| 21 | Sat 27 Apr 2019 | 3-2 v CowdenbeathAnnan Athletic 3-2 Cowdenbeath | Ladbrokes League Two |
| 22 | Sat 4 May 2019 | 2-0 v Albion RoversAlbion Rovers 0-2 Annan Athletic | Ladbrokes League Two |
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