| 1 | Sat 10 Aug 2019 | 0-1 v Forfar AthleticForfar Athletic 1-0 Stranraer | Ladbrokes League One |
| 2 | Sat 17 Aug 2019 | 3-2 v Raith RoversStranraer 3-2 Raith Rovers | Ladbrokes League One |
| 3 | Sat 24 Aug 2019 | 1-3 v DumbartonDumbarton 3-1 Stranraer | Ladbrokes League One |
| 4 | Sat 31 Aug 2019 | 1-2 v PeterheadStranraer 1-2 Peterhead | Ladbrokes League One |
| 5 | Sat 14 Sep 2019 | 1-6 v ClydeClyde 6-1 Stranraer | Ladbrokes League One |
| 6 | Sat 21 Sep 2019 | 0-3 v FalkirkStranraer 0-3 Falkirk | Ladbrokes League One |
| 7 | Sat 28 Sep 2019 | 2-2 v AirdrieoniansAirdrieonians 2-2 Stranraer | Ladbrokes League One |
| 8 | Sat 5 Oct 2019 | 1-1 v East FifeEast Fife 1-1 Stranraer | Ladbrokes League One |
| 9 | Sat 19 Oct 2019 | 0-0 v DumbartonStranraer 0-0 Dumbarton | Ladbrokes League One |
| 10 | Sat 26 Oct 2019 | 1-2 v MontroseMontrose 2-1 Stranraer | Ladbrokes League One |
| 11 | Sat 2 Nov 2019 | 3-0 v ClydeStranraer 3-0 Clyde | Ladbrokes League One |
| 12 | Sat 9 Nov 2019 | 1-3 v Raith RoversRaith Rovers 3-1 Stranraer | Ladbrokes League One |
| 13 | Sat 16 Nov 2019 | 0-2 v AirdrieoniansStranraer 0-2 Airdrieonians | Ladbrokes League One |
| 14 | Sat 30 Nov 2019 | 0-3 v FalkirkFalkirk 3-0 Stranraer | Ladbrokes League One |
| 15 | Sat 7 Dec 2019 | 0-3 v PeterheadPeterhead 3-0 Stranraer | Ladbrokes League One |
| 16 | Sat 14 Dec 2019 | 0-2 v East FifeStranraer 0-2 East Fife | Ladbrokes League One |
| 17 | Sat 21 Dec 2019 | 2-4 v Forfar AthleticStranraer 2-4 Forfar Athletic | Ladbrokes League One |
| 18 | Fri 17 Jan 2020 | 0-2 v RangersRangers 2-0 Stranraer | William Hill Scottish Cup Fourth Round |
| 19 | Sat 25 Jan 2020 | 0-0 v AirdrieoniansAirdrieonians 0-0 Stranraer | Ladbrokes League One |
| 20 | Sat 1 Feb 2020 | 1-1 v FalkirkStranraer 1-1 Falkirk | Ladbrokes League One |
| 21 | Sat 8 Feb 2020 | 1-1 v Raith RoversStranraer 1-1 Raith Rovers | Ladbrokes League One |
| 22 | Sat 15 Feb 2020 | 1-1 v Forfar AthleticForfar Athletic 1-1 Stranraer | Ladbrokes League One |
| 23 | Sat 22 Feb 2020 | 2-4 v East FifeEast Fife 4-2 Stranraer | Ladbrokes League One |
| 24 | Sat 7 Mar 2020 | 1-4 v MontroseMontrose 4-1 Stranraer | Ladbrokes League One |
| 25 | Tue 10 Mar 2020 | 0-1 v MontroseStranraer 0-1 Montrose | Ladbrokes League One |
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