| 1 | Sat 17 Aug 2019 | 101-2 v Nantwich TownNantwich Town 2-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 2 | Sat 24 Aug 2019 | 100-0 v Warrington TownGainsborough Trinity 0-0 Warrington Town | BetVictor Northern Premier Division |
| 3 | Mon 26 Aug 2019 | 151-2 v Matlock TownMatlock Town 2-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 4 | Tue 10 Sep 2019 | 91-0 v Banbury UnitedGainsborough Trinity 1-0 Banbury United | Emirates FA Cup First Qualifying Round Replay |
| 5 | Sat 14 Sep 2019 | 100-1 v Witton AlbionWitton Albion 1-0 Gainsborough Trinity | BetVictor Northern Premier Division |
| 6 | Sat 21 Sep 2019 | 100-2 v Rushall OlympicRushall Olympic 2-0 Gainsborough Trinity | Emirates FA Cup Second Qualifying Round |
| 7 | Tue 24 Sep 2019 | 140-2 v South ShieldsSouth Shields 2-0 Gainsborough Trinity | BetVictor Northern Premier Division |
| 8 | Sat 28 Sep 2019 | 102-2 v Mickleover SportsGainsborough Trinity 2-2 Mickleover Sports | BetVictor Northern Premier Division |
| 9 | Tue 1 Oct 2019 | 9 4-1 v Bamber BridgeGainsborough Trinity 4-1 Bamber Bridge | BetVictor Northern Premier Division |
| 10 | Sat 5 Oct 2019 | 93-4 v Basford UnitedBasford United 4-3 Gainsborough Trinity | BetVictor Northern Premier Division |
| 11 | Tue 15 Oct 2019 | 100-0 v BuxtonGainsborough Trinity 0-0 Buxton | BetVictor Northern Premier Division |
| 12 | Sat 19 Oct 2019 | 101-3 v Ashton UnitedAshton United 3-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 13 | Tue 29 Oct 2019 | 94-0 v DunstonDunston 0-4 Gainsborough Trinity | Buildbase FA Trophy First Qualifying Round |
| 14 | Sat 2 Nov 2019 | 9 2-2 v FC United of ManchesterFC United of Manchester 2-2 Gainsborough Trinity | BetVictor Northern Premier Division |
| 15 | Sat 16 Nov 2019 | 90-1 v Morpeth TownGainsborough Trinity 0-1 Morpeth Town | BetVictor Northern Premier Division |
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