| 1 | Sat 17 Aug 2019 | 121-2 v Nantwich TownNantwich Town 2-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 2 | Mon 26 Aug 2019 | 101-2 v Matlock TownMatlock Town 2-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 3 | Sat 31 Aug 2019 | 102-4 v Lancaster CityGainsborough Trinity 2-4 Lancaster City | BetVictor Northern Premier Division |
| 4 | Sat 7 Sep 2019 | 152-2 v Banbury UnitedBanbury United 2-2 Gainsborough Trinity | Emirates FA Cup First Qualifying Round |
| 5 | Tue 10 Sep 2019 | 151-0 v Banbury UnitedGainsborough Trinity 1-0 Banbury United | Emirates FA Cup First Qualifying Round Replay |
| 6 | Sat 14 Sep 2019 | 140-1 v Witton AlbionWitton Albion 1-0 Gainsborough Trinity | BetVictor Northern Premier Division |
| 7 | Tue 24 Sep 2019 | 10 0-2 v South ShieldsSouth Shields 2-0 Gainsborough Trinity | BetVictor Northern Premier Division |
| 8 | Sat 28 Sep 2019 | 112-2 v Mickleover SportsGainsborough Trinity 2-2 Mickleover Sports | BetVictor Northern Premier Division |
| 9 | Tue 1 Oct 2019 | 104-1 v Bamber BridgeGainsborough Trinity 4-1 Bamber Bridge | BetVictor Northern Premier Division |
| 10 | Sat 5 Oct 2019 | 103-4 v Basford UnitedBasford United 4-3 Gainsborough Trinity | BetVictor Northern Premier Division |
| 11 | Sat 12 Oct 2019 | 100-2 v Atherton CollieriesGainsborough Trinity 0-2 Atherton Collieries | BetVictor Northern Premier Division |
| 12 | Tue 15 Oct 2019 | 70-0 v BuxtonGainsborough Trinity 0-0 Buxton | BetVictor Northern Premier Division |
| 13 | Sat 19 Oct 2019 | 71-3 v Ashton UnitedAshton United 3-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 14 | Tue 29 Oct 2019 | 174-0 v DunstonDunston 0-4 Gainsborough Trinity | Buildbase FA Trophy First Qualifying Round |
| 15 | Sat 2 Nov 2019 | 162-2 v FC United of ManchesterFC United of Manchester 2-2 Gainsborough Trinity | BetVictor Northern Premier Division |
| 16 | Sat 9 Nov 2019 | 95-3 v TamworthTamworth 3-5 Gainsborough Trinity | Buildbase FA Trophy Second Qualifying Round |
| 17 | Sat 7 Dec 2019 | 172-3 v Scarborough AthleticGainsborough Trinity 2-3 Scarborough Athletic | BetVictor Northern Premier Division |
| 18 | Sat 14 Dec 2019 | 101-1 v Hyde UnitedHyde United 1-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 19 | Sat 21 Dec 2019 | 160-0 v Nantwich TownGainsborough Trinity 0-0 Nantwich Town | BetVictor Northern Premier Division |
| 20 | Thu 26 Dec 2019 | 145-1 v Grantham TownGrantham Town 1-5 Gainsborough Trinity | BetVictor Northern Premier Division |
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