| 1 | Sat 12 Jan 2019 | 1-2 v Forfar AthleticForfar Athletic 2-1 Stranraer | Ladbrokes League One |
| 2 | Sat 19 Jan 2019 | 1-4 v Partick ThistlePartick Thistle 4-1 Stranraer | William Hill Scottish Cup Fourth Round |
| 3 | Sat 26 Jan 2019 | 3-4 v East FifeStranraer 3-4 East Fife | Ladbrokes League One |
| 4 | Tue 12 Feb 2019 | 1-1 v ArbroathArbroath 1-1 Stranraer | Ladbrokes League One |
| 5 | Sat 16 Feb 2019 | 0-3 v DumbartonStranraer 0-3 Dumbarton | Ladbrokes League One |
| 6 | Tue 26 Feb 2019 | 1-1 v StenhousemuirStranraer 1-1 Stenhousemuir | Ladbrokes League One |
| 7 | Sat 2 Mar 2019 | 2-2 v Raith RoversStranraer 2-2 Raith Rovers | Ladbrokes League One |
| 8 | Sat 16 Mar 2019 | 1-0 v StenhousemuirStenhousemuir 0-1 Stranraer | Ladbrokes League One |
| 9 | Tue 26 Mar 2019 | 0-2 v Brechin CityStranraer 0-2 Brechin City | Ladbrokes League One |
| 10 | Sat 30 Mar 2019 | 1-3 v MontroseMontrose 3-1 Stranraer | Ladbrokes League One |
| 11 | Sat 6 Apr 2019 | 2-1 v Forfar AthleticStranraer 2-1 Forfar Athletic | Ladbrokes League One |
| 12 | Sat 4 May 2019 | 1-4 v AirdrieoniansStranraer 1-4 Airdrieonians | Ladbrokes League One |
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