| 1 | Sat 17 Aug 2019 | 21-2 v Nantwich TownNantwich Town 2-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 2 | Sat 24 Aug 2019 | 20-0 v Warrington TownGainsborough Trinity 0-0 Warrington Town | BetVictor Northern Premier Division |
| 3 | Mon 26 Aug 2019 | 21-2 v Matlock TownMatlock Town 2-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 4 | Sat 31 Aug 2019 | 22-4 v Lancaster CityGainsborough Trinity 2-4 Lancaster City | BetVictor Northern Premier Division |
| 5 | Sat 7 Sep 2019 | 22-2 v Banbury UnitedBanbury United 2-2 Gainsborough Trinity | Emirates FA Cup First Qualifying Round |
| 6 | Tue 10 Sep 2019 | 21-0 v Banbury UnitedGainsborough Trinity 1-0 Banbury United | Emirates FA Cup First Qualifying Round Replay |
| 7 | Sat 14 Sep 2019 | 20-1 v Witton AlbionWitton Albion 1-0 Gainsborough Trinity | BetVictor Northern Premier Division |
| 8 | Sat 21 Sep 2019 | 20-2 v Rushall OlympicRushall Olympic 2-0 Gainsborough Trinity | Emirates FA Cup Second Qualifying Round |
| 9 | Tue 24 Sep 2019 | 160-2 v South ShieldsSouth Shields 2-0 Gainsborough Trinity | BetVictor Northern Premier Division |
| 10 | Tue 1 Oct 2019 | 154-1 v Bamber BridgeGainsborough Trinity 4-1 Bamber Bridge | BetVictor Northern Premier Division |
| 11 | Sat 5 Oct 2019 | 153-4 v Basford UnitedBasford United 4-3 Gainsborough Trinity | BetVictor Northern Premier Division |
| 12 | Sat 12 Oct 2019 | 20-2 v Atherton CollieriesGainsborough Trinity 0-2 Atherton Collieries | BetVictor Northern Premier Division |
| 13 | Sat 19 Oct 2019 | 161-3 v Ashton UnitedAshton United 3-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 14 | Tue 29 Oct 2019 | 24-0 v DunstonDunston 0-4 Gainsborough Trinity | Buildbase FA Trophy First Qualifying Round |
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