| 1 | Sat 6 Oct 2018 | 3-1 v AirdrieoniansAirdrieonians 1-3 Brechin City | Ladbrokes League One |
| 2 | Sat 20 Oct 2018 | 1-3 v East FifeEast Fife 3-1 Brechin City | Ladbrokes League One |
| 3 | Sat 3 Nov 2018 | 1-2 v Raith RoversRaith Rovers 2-1 Brechin City | Ladbrokes League One |
| 4 | Sat 10 Nov 2018 | 4-0 v Forfar AthleticBrechin City 4-0 Forfar Athletic | Ladbrokes League One |
| 5 | Sat 17 Nov 2018 | 1-5 v ArbroathBrechin City 1-5 Arbroath | Ladbrokes League One |
| 6 | Sat 29 Dec 2018 | 0-2 v Forfar AthleticForfar Athletic 2-0 Brechin City | Ladbrokes League One |
| 7 | Sat 23 Feb 2019 | 0-3 v Elgin CityBerwick Rangers 0-3 Elgin City | Ladbrokes League Two |
| 8 | Tue 26 Feb 2019 | 1-2 v Annan AthleticBerwick Rangers 1-2 Annan Athletic | Ladbrokes League Two |
| 9 | Sat 2 Mar 2019 | 1-1 v Albion RoversAlbion Rovers 1-1 Berwick Rangers | Ladbrokes League Two |
| 10 | Tue 5 Mar 2019 | 0-1 v Edinburgh CityEdinburgh City 1-0 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 13 Apr 2019 | 0-3 v Queens ParkBerwick Rangers 0-3 Queens Park | Ladbrokes League Two |
| 18 | Sat 20 Apr 2019 | 0-5 v ClydeClyde 5-0 Berwick Rangers | Ladbrokes League Two |
| 19 | Sat 27 Apr 2019 | 0-3 v Albion RoversBerwick Rangers 0-3 Albion Rovers | 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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