| 1 | 14/7/2018 | 3-5 v Queen of the SouthQueen of the South 5-3 Stranraer | Betfred Cup Group G |
| 2 | 24/7/2018 | 1-3 v ClydeStranraer 1-3 Clyde | Betfred Cup Group G |
| 3 | 11/8/2018 | 1-3 v ArbroathArbroath 3-1 Stranraer | Ladbrokes League One |
| 4 | 14/8/2018 | 0-5 v Partick ThistleStranraer 0-5 Partick Thistle | IRN-BRU Cup First Round |
| 5 | 18/8/2018 | 0-0 v Forfar AthleticForfar Athletic 0-0 Stranraer | Ladbrokes League One |
| 6 | 25/8/2018 | 2-0 v MontroseStranraer 2-0 Montrose | Ladbrokes League One |
| 7 | 1/9/2018 | 0-2 v AirdrieoniansAirdrieonians 2-0 Stranraer | Ladbrokes League One |
| 8 | 15/9/2018 | 2-0 v StenhousemuirStranraer 2-0 Stenhousemuir | Ladbrokes League One |
| 9 | 29/9/2018 | 1-1 v Brechin CityBrechin City 1-1 Stranraer | Ladbrokes League One |
| 10 | 6/10/2018 | 3-2 v DumbartonStranraer 3-2 Dumbarton | Ladbrokes League One |
| 11 | 27/10/2018 | 0-1 v ArbroathStranraer 0-1 Arbroath | Ladbrokes League One |
| 12 | 3/11/2018 | 2-0 v StenhousemuirStenhousemuir 0-2 Stranraer | Ladbrokes League One |
| 13 | 10/11/2018 | 1-2 v AirdrieoniansStranraer 1-2 Airdrieonians | Ladbrokes League One |
| 14 | 17/11/2018 | 1-1 v MontroseMontrose 1-1 Stranraer | Ladbrokes League One |
| 15 | 24/11/2018 | 1-0 v ArbroathArbroath 0-1 Stranraer | William Hill Scottish Cup Third Round |
| 16 | 1/12/2018 | 2-1 v Forfar AthleticStranraer 2-1 Forfar Athletic | Ladbrokes League One |
| 17 | 8/12/2018 | 3-3 v East FifeEast Fife 3-3 Stranraer | Ladbrokes League One |
| 18 | 22/12/2018 | 1-0 v DumbartonDumbarton 0-1 Stranraer | Ladbrokes League One |
| 19 | 29/12/2018 | 0-3 v AirdrieoniansAirdrieonians 3-0 Stranraer | Ladbrokes League One |
| 20 | 5/1/2019 | 1-2 v MontroseStranraer 1-2 Montrose | Ladbrokes League One |
| 21 | 12/1/2019 | 1-2 v Forfar AthleticForfar Athletic 2-1 Stranraer | Ladbrokes League One |
| 22 | 19/1/2019 | 1-4 v Partick ThistlePartick Thistle 4-1 Stranraer | William Hill Scottish Cup Fourth Round |
| 23 | 26/1/2019 | 3-4 v East FifeStranraer 3-4 East Fife | Ladbrokes League One |
| 24 | 12/2/2019 | 1-1 v ArbroathArbroath 1-1 Stranraer | Ladbrokes League One |
| 25 | 16/2/2019 | 0-3 v DumbartonStranraer 0-3 Dumbarton | Ladbrokes League One |
| 26 | 23/2/2019 | 2-1 v Brechin CityBrechin City 1-2 Stranraer | Ladbrokes League One |
| 27 | 26/2/2019 | 1-1 v StenhousemuirStranraer 1-1 Stenhousemuir | Ladbrokes League One |
| 28 | 2/3/2019 | 2-2 v Raith RoversStranraer 2-2 Raith Rovers | Ladbrokes League One |
| 29 | 9/3/2019 | 1-3 v East FifeEast Fife 3-1 Stranraer | Ladbrokes League One |
| 30 | 16/3/2019 | 1-0 v StenhousemuirStenhousemuir 0-1 Stranraer | Ladbrokes League One |
| 31 | 23/3/2019 | 0-0 v ArbroathStranraer 0-0 Arbroath | Ladbrokes League One |
| 32 | 26/3/2019 | 0-2 v Brechin CityStranraer 0-2 Brechin City | Ladbrokes League One |
| 33 | 30/3/2019 | 1-3 v MontroseMontrose 3-1 Stranraer | Ladbrokes League One |
| 34 | 6/4/2019 | 2-1 v Forfar AthleticStranraer 2-1 Forfar Athletic | Ladbrokes League One |
| 35 | 13/4/2019 | 3-2 v Raith RoversRaith Rovers 2-3 Stranraer | Ladbrokes League One |
| 36 | 20/4/2019 | 3-0 v Brechin CityStranraer 3-0 Brechin City | Ladbrokes League One |
| 37 | 27/4/2019 | 1-2 v DumbartonDumbarton 2-1 Stranraer | Ladbrokes League One |
