| 1 | Sat 17 Aug 2019 | 141-2 v Nantwich TownNantwich Town 2-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 2 | Mon 26 Aug 2019 | 141-2 v Matlock TownMatlock Town 2-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 3 | Sat 31 Aug 2019 | 112-4 v Lancaster CityGainsborough Trinity 2-4 Lancaster City | BetVictor Northern Premier Division |
| 4 | Sat 7 Sep 2019 | 112-2 v Banbury UnitedBanbury United 2-2 Gainsborough Trinity | Emirates FA Cup First Qualifying Round |
| 5 | Tue 10 Sep 2019 | 11 1-0 v Banbury UnitedGainsborough Trinity 1-0 Banbury United | Emirates FA Cup First Qualifying Round Replay |
| 6 | Sat 14 Sep 2019 | 110-1 v Witton AlbionWitton Albion 1-0 Gainsborough Trinity | BetVictor Northern Premier Division |
| 7 | Sat 21 Sep 2019 | 120-2 v Rushall OlympicRushall Olympic 2-0 Gainsborough Trinity | Emirates FA Cup Second Qualifying Round |
| 8 | Tue 24 Sep 2019 | 110-2 v South ShieldsSouth Shields 2-0 Gainsborough Trinity | BetVictor Northern Premier Division |
| 9 | Sat 28 Sep 2019 | 142-2 v Mickleover SportsGainsborough Trinity 2-2 Mickleover Sports | BetVictor Northern Premier Division |
| 10 | Tue 1 Oct 2019 | 74-1 v Bamber BridgeGainsborough Trinity 4-1 Bamber Bridge | BetVictor Northern Premier Division |
| 11 | Sat 5 Oct 2019 | 73-4 v Basford UnitedBasford United 4-3 Gainsborough Trinity | BetVictor Northern Premier Division |
| 12 | Sat 12 Oct 2019 | 90-2 v Atherton CollieriesGainsborough Trinity 0-2 Atherton Collieries | BetVictor Northern Premier Division |
| 13 | Tue 15 Oct 2019 | 110-0 v BuxtonGainsborough Trinity 0-0 Buxton | BetVictor Northern Premier Division |
| 14 | Sat 19 Oct 2019 | 111-3 v Ashton UnitedAshton United 3-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 15 | Tue 29 Oct 2019 | 114-0 v DunstonDunston 0-4 Gainsborough Trinity | Buildbase FA Trophy First Qualifying Round |
| 16 | Sat 2 Nov 2019 | 72-2 v FC United of ManchesterFC United of Manchester 2-2 Gainsborough Trinity | BetVictor Northern Premier Division |
| 17 | Sat 9 Nov 2019 | 75-3 v TamworthTamworth 3-5 Gainsborough Trinity | Buildbase FA Trophy Second Qualifying Round |
| 18 | Sat 16 Nov 2019 | 70-1 v Morpeth TownGainsborough Trinity 0-1 Morpeth Town | BetVictor Northern Premier Division |
| 19 | Sat 7 Dec 2019 | 72-3 v Scarborough AthleticGainsborough Trinity 2-3 Scarborough Athletic | BetVictor Northern Premier Division |
| 20 | Sat 14 Dec 2019 | 161-1 v Hyde UnitedHyde United 1-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 21 | Sat 21 Dec 2019 | 150-0 v Nantwich TownGainsborough Trinity 0-0 Nantwich Town | BetVictor Northern Premier Division |
| 22 | Thu 26 Dec 2019 | 115-1 v Grantham TownGrantham Town 1-5 Gainsborough Trinity | BetVictor Northern Premier Division |
| 23 | Wed 1 Jan 2020 | 112-1 v Matlock TownGainsborough Trinity 2-1 Matlock Town | BetVictor Northern Premier Division |
| 24 | Sat 18 Jan 2020 | 142-0 v RadcliffeRadcliffe 0-2 Gainsborough Trinity | BetVictor Northern Premier Division |
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