| 1 | Sat 22 Dec 2018 | 0-4 v Annan AthleticAnnan Athletic 4-0 Berwick Rangers | Ladbrokes League Two |
| 2 | Sat 29 Dec 2018 | 2-2 v Edinburgh CityBerwick Rangers 2-2 Edinburgh City | Ladbrokes League Two |
| 3 | Sat 5 Jan 2019 | 0-2 v CowdenbeathCowdenbeath 2-0 Berwick Rangers | Ladbrokes League Two |
| 4 | Sat 12 Jan 2019 | 0-3 v ClydeBerwick Rangers 0-3 Clyde | Ladbrokes League Two |
| 5 | Sat 19 Jan 2019 | 0-2 v PeterheadPeterhead 2-0 Berwick Rangers | Ladbrokes League Two |
| 6 | Sat 26 Jan 2019 | 1-7 v Queens ParkQueens Park 7-1 Berwick Rangers | Ladbrokes League Two |
| 7 | Sat 9 Feb 2019 | 1-2 v Stirling AlbionBerwick Rangers 1-2 Stirling Albion | Ladbrokes League Two |
| 8 | Sat 23 Feb 2019 | 0-3 v Elgin CityBerwick Rangers 0-3 Elgin City | Ladbrokes League Two |
| 9 | Tue 26 Feb 2019 | 1-2 v Annan AthleticBerwick Rangers 1-2 Annan Athletic | Ladbrokes League Two |
| 10 | Sat 2 Mar 2019 | 1-1 v Albion RoversAlbion Rovers 1-1 Berwick Rangers | Ladbrokes League Two |
| 11 | Sat 9 Mar 2019 | 1-1 v CowdenbeathBerwick Rangers 1-1 Cowdenbeath | Ladbrokes League Two |
| 12 | Tue 12 Mar 2019 | 1-2 v Queens ParkBerwick Rangers 1-2 Queens Park | Ladbrokes League Two |
| 13 | Tue 19 Mar 2019 | 2-0 v PeterheadBerwick Rangers 2-0 Peterhead | Ladbrokes League Two |
| 14 | Sat 23 Mar 2019 | 0-1 v Stirling AlbionStirling Albion 1-0 Berwick Rangers | Ladbrokes League Two |
| 15 | Sat 30 Mar 2019 | 0-2 v Edinburgh CityBerwick Rangers 0-2 Edinburgh City | Ladbrokes League Two |
| 16 | Sat 6 Apr 2019 | 0-6 v Annan AthleticAnnan Athletic 6-0 Berwick Rangers | Ladbrokes League Two |
| 17 | Sat 20 Apr 2019 | 0-5 v ClydeClyde 5-0 Berwick Rangers | Ladbrokes League Two |
| 18 | Sat 27 Apr 2019 | 0-3 v Albion RoversBerwick Rangers 0-3 Albion Rovers | Ladbrokes League Two |
| 19 | Sat 4 May 2019 | 0-2 v Elgin CityElgin City 2-0 Berwick Rangers | Ladbrokes League Two |
| 20 | Sat 11 May 2019 | 0-4 v Cove RangersCove Rangers 4-0 Berwick Rangers | Ladbrokes League Two Play-off Final |
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