| 1 | Sat 22 Dec 2018 | 4-0 v Berwick RangersAnnan Athletic 4-0 Berwick Rangers | Ladbrokes League Two |
| 2 | Sat 29 Dec 2018 | 1-1 v Albion RoversAlbion Rovers 1-1 Annan Athletic | Ladbrokes League Two |
| 3 | Sat 16 Feb 2019 | 4-2 v CowdenbeathCowdenbeath 2-4 Annan Athletic | Ladbrokes League Two |
| 4 | Sat 23 Feb 2019 | 4-0 v Albion RoversAnnan Athletic 4-0 Albion Rovers | Ladbrokes League Two |
| 5 | Tue 26 Feb 2019 | 2-1 v Berwick RangersBerwick Rangers 1-2 Annan Athletic | Ladbrokes League Two |
| 6 | Sat 2 Mar 2019 | 2-1 v Queens ParkAnnan Athletic 2-1 Queens Park | Ladbrokes League Two |
| 7 | Sat 9 Mar 2019 | 1-2 v PeterheadPeterhead 2-1 Annan Athletic | Ladbrokes League Two |
| 8 | Sat 16 Mar 2019 | 3-1 v Edinburgh CityAnnan Athletic 3-1 Edinburgh City | Ladbrokes League Two |
| 9 | Sat 23 Mar 2019 | 1-2 v ClydeClyde 2-1 Annan Athletic | Ladbrokes League Two |
| 10 | Sat 6 Apr 2019 | 6-0 v Berwick RangersAnnan Athletic 6-0 Berwick Rangers | Ladbrokes League Two |
| 11 | Sat 13 Apr 2019 | 2-2 v Stirling AlbionAnnan Athletic 2-2 Stirling Albion | Ladbrokes League Two |
| 12 | Sat 27 Apr 2019 | 3-2 v CowdenbeathAnnan Athletic 3-2 Cowdenbeath | Ladbrokes League Two |
| 13 | Sat 4 May 2019 | 2-0 v Albion RoversAlbion Rovers 0-2 Annan Athletic | Ladbrokes League Two |
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