1 | Sat 9 Feb 2019 | 1-1 v ClydeAnnan Athletic 1-1 Clyde | Ladbrokes League Two |
2 | Sat 16 Feb 2019 | 4-2 v CowdenbeathCowdenbeath 2-4 Annan Athletic | Ladbrokes League Two |
3 | Sat 23 Feb 2019 | 4-0 v Albion RoversAnnan Athletic 4-0 Albion Rovers | Ladbrokes League Two |
4 | Tue 26 Feb 2019 | 2-1 v Berwick RangersBerwick Rangers 1-2 Annan Athletic | Ladbrokes League Two |
5 | Sat 2 Mar 2019 | 2-1 v Queens ParkAnnan Athletic 2-1 Queens Park | Ladbrokes League Two |
6 | Sat 9 Mar 2019 | 1-2 v PeterheadPeterhead 2-1 Annan Athletic | Ladbrokes League Two |
7 | Sat 16 Mar 2019 | 3-1 v Edinburgh CityAnnan Athletic 3-1 Edinburgh City | Ladbrokes League Two |
8 | Sat 30 Mar 2019 | 1-0 v Elgin CityElgin City 0-1 Annan Athletic | Ladbrokes League Two |
9 | Sat 6 Apr 2019 | 6-0 v Berwick RangersAnnan Athletic 6-0 Berwick Rangers | Ladbrokes League Two |
10 | Sat 13 Apr 2019 | 2-2 v Stirling AlbionAnnan Athletic 2-2 Stirling Albion | Ladbrokes League Two |
11 | Sat 20 Apr 2019 | 3-0 v Queens ParkQueens Park 0-3 Annan Athletic | Ladbrokes League Two |
12 | Sat 27 Apr 2019 | 3-2 v CowdenbeathAnnan Athletic 3-2 Cowdenbeath | Ladbrokes League Two |