| 1 | 17/8/2019 | 51-2 v Nantwich TownNantwich Town 2-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 2 | 24/8/2019 | 50-0 v Warrington TownGainsborough Trinity 0-0 Warrington Town | BetVictor Northern Premier Division |
| 3 | 26/8/2019 | 51-2 v Matlock TownMatlock Town 2-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 4 | 31/8/2019 | 52-4 v Lancaster CityGainsborough Trinity 2-4 Lancaster City | BetVictor Northern Premier Division |
| 5 | 7/9/2019 | 5 2-2 v Banbury UnitedBanbury United 2-2 Gainsborough Trinity | Emirates FA Cup First Qualifying Round |
| 6 | 10/9/2019 | 51-0 v Banbury UnitedGainsborough Trinity 1-0 Banbury United | Emirates FA Cup First Qualifying Round Replay |
| 7 | 14/9/2019 | 50-1 v Witton AlbionWitton Albion 1-0 Gainsborough Trinity | BetVictor Northern Premier Division |
| 8 | 21/9/2019 | 160-2 v Rushall OlympicRushall Olympic 2-0 Gainsborough Trinity | Emirates FA Cup Second Qualifying Round |
| 9 | 24/9/2019 | 50-2 v South ShieldsSouth Shields 2-0 Gainsborough Trinity | BetVictor Northern Premier Division |
| 10 | 28/9/2019 | 122-2 v Mickleover SportsGainsborough Trinity 2-2 Mickleover Sports | BetVictor Northern Premier Division |
| 11 | 1/10/2019 | 124-1 v Bamber BridgeGainsborough Trinity 4-1 Bamber Bridge | BetVictor Northern Premier Division |
| 12 | 5/10/2019 | 123-4 v Basford UnitedBasford United 4-3 Gainsborough Trinity | BetVictor Northern Premier Division |
| 13 | 12/10/2019 | 50-2 v Atherton CollieriesGainsborough Trinity 0-2 Atherton Collieries | BetVictor Northern Premier Division |
| 14 | 15/10/2019 | 50-0 v BuxtonGainsborough Trinity 0-0 Buxton | BetVictor Northern Premier Division |
| 15 | 19/10/2019 | 51-3 v Ashton UnitedAshton United 3-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 16 | 29/10/2019 | 5 4-0 v DunstonDunston 0-4 Gainsborough Trinity | Buildbase FA Trophy First Qualifying Round |
| 17 | 9/11/2019 | 125-3 v TamworthTamworth 3-5 Gainsborough Trinity | Buildbase FA Trophy Second Qualifying Round |
| 18 | 16/11/2019 | 120-1 v Morpeth TownGainsborough Trinity 0-1 Morpeth Town | BetVictor Northern Premier Division |
| 19 | 7/12/2019 | 62-3 v Scarborough AthleticGainsborough Trinity 2-3 Scarborough Athletic | BetVictor Northern Premier Division |
