| 1 | Mon 26 Aug 2019 | 121-2 v Matlock TownMatlock Town 2-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 2 | Sat 31 Aug 2019 | 142-4 v Lancaster CityGainsborough Trinity 2-4 Lancaster City | BetVictor Northern Premier Division |
| 3 | Tue 10 Sep 2019 | 141-0 v Banbury UnitedGainsborough Trinity 1-0 Banbury United | Emirates FA Cup First Qualifying Round Replay |
| 4 | Sat 14 Sep 2019 | 15 0-1 v Witton AlbionWitton Albion 1-0 Gainsborough Trinity | BetVictor Northern Premier Division |
| 5 | Tue 17 Sep 2019 | 90-0 v Spalding UnitedSpalding United 0-0 Gainsborough Trinity | Integro League Cup First Round |
| 6 | Sat 21 Sep 2019 | 150-2 v Rushall OlympicRushall Olympic 2-0 Gainsborough Trinity | Emirates FA Cup Second Qualifying Round |
| 7 | Tue 24 Sep 2019 | 120-2 v South ShieldsSouth Shields 2-0 Gainsborough Trinity | BetVictor Northern Premier Division |
| 8 | Sat 28 Sep 2019 | 72-2 v Mickleover SportsGainsborough Trinity 2-2 Mickleover Sports | BetVictor Northern Premier Division |
| 9 | Tue 1 Oct 2019 | 144-1 v Bamber BridgeGainsborough Trinity 4-1 Bamber Bridge | BetVictor Northern Premier Division |
| 10 | Sat 5 Oct 2019 | 143-4 v Basford UnitedBasford United 4-3 Gainsborough Trinity | BetVictor Northern Premier Division |
| 11 | Sat 12 Oct 2019 | 120-2 v Atherton CollieriesGainsborough Trinity 0-2 Atherton Collieries | BetVictor Northern Premier Division |
| 12 | Tue 29 Oct 2019 | 164-0 v DunstonDunston 0-4 Gainsborough Trinity | Buildbase FA Trophy First Qualifying Round |
| 13 | Sat 9 Nov 2019 | 115-3 v TamworthTamworth 3-5 Gainsborough Trinity | Buildbase FA Trophy Second Qualifying Round |
| 14 | Sat 16 Nov 2019 | 110-1 v Morpeth TownGainsborough Trinity 0-1 Morpeth Town | BetVictor Northern Premier Division |
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