| 1 | Sat 2 Nov 2019 | 12-2 v FC United of ManchesterFC United of Manchester 2-2 Gainsborough Trinity | BetVictor Northern Premier Division |
| 2 | Sat 9 Nov 2019 | 1 5-3 v TamworthTamworth 3-5 Gainsborough Trinity | Buildbase FA Trophy Second Qualifying Round |
| 3 | Sat 16 Nov 2019 | 1 0-1 v Morpeth TownGainsborough Trinity 0-1 Morpeth Town | BetVictor Northern Premier Division |
| 4 | Sat 7 Dec 2019 | 12-3 v Scarborough AthleticGainsborough Trinity 2-3 Scarborough Athletic | BetVictor Northern Premier Division |
| 5 | Sat 14 Dec 2019 | 11-1 v Hyde UnitedHyde United 1-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 6 | Sat 21 Dec 2019 | 10-0 v Nantwich TownGainsborough Trinity 0-0 Nantwich Town | BetVictor Northern Premier Division |
| 7 | Thu 26 Dec 2019 | 15-1 v Grantham TownGrantham Town 1-5 Gainsborough Trinity | BetVictor Northern Premier Division |
| 8 | Wed 1 Jan 2020 | 12-1 v Matlock TownGainsborough Trinity 2-1 Matlock Town | BetVictor Northern Premier Division |
| 9 | Sat 4 Jan 2020 | 12-2 v Whitby TownWhitby Town 2-2 Gainsborough Trinity | BetVictor Northern Premier Division |
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