| 1 | Mon 26 Aug 2019 | 81-2 v Matlock TownMatlock Town 2-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 2 | Sat 19 Oct 2019 | 12 1-3 v Ashton UnitedAshton United 3-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 3 | Tue 29 Oct 2019 | 154-0 v DunstonDunston 0-4 Gainsborough Trinity | Buildbase FA Trophy First Qualifying Round |
| 4 | Sat 2 Nov 2019 | 142-2 v FC United of ManchesterFC United of Manchester 2-2 Gainsborough Trinity | BetVictor Northern Premier Division |
| 5 | Sat 9 Nov 2019 | 155-3 v TamworthTamworth 3-5 Gainsborough Trinity | Buildbase FA Trophy Second Qualifying Round |
| 6 | Sat 16 Nov 2019 | 100-1 v Morpeth TownGainsborough Trinity 0-1 Morpeth Town | BetVictor Northern Premier Division |
| 7 | Sat 14 Dec 2019 | 121-1 v Hyde UnitedHyde United 1-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 8 | Sat 21 Dec 2019 | 80-0 v Nantwich TownGainsborough Trinity 0-0 Nantwich Town | BetVictor Northern Premier Division |
| 9 | Thu 26 Dec 2019 | 45-1 v Grantham TownGrantham Town 1-5 Gainsborough Trinity | BetVictor Northern Premier Division |
| 10 | Wed 1 Jan 2020 | 42-1 v Matlock TownGainsborough Trinity 2-1 Matlock Town | BetVictor Northern Premier Division |
| 11 | Sat 25 Jan 2020 | 143-1 v Atherton CollieriesAtherton Collieries 1-3 Gainsborough Trinity | BetVictor Northern Premier Division |
| 12 | Sat 8 Feb 2020 | 143-3 v BuxtonBuxton 3-3 Gainsborough Trinity | BetVictor Northern Premier Division |
| 13 | Tue 18 Feb 2020 | 101-1 v Kidsgrove AthleticGainsborough Trinity 1-1 Kidsgrove Athletic | Integro League Cup Third Round |
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