| 1 | Sat 7 Dec 2019 | 92-3 v Scarborough AthleticGainsborough Trinity 2-3 Scarborough Athletic | BetVictor Northern Premier Division |
| 2 | Sat 14 Dec 2019 | 91-1 v Hyde UnitedHyde United 1-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 3 | Sat 21 Dec 2019 | 90-0 v Nantwich TownGainsborough Trinity 0-0 Nantwich Town | BetVictor Northern Premier Division |
| 4 | Thu 26 Dec 2019 | 105-1 v Grantham TownGrantham Town 1-5 Gainsborough Trinity | BetVictor Northern Premier Division |
| 5 | Wed 1 Jan 2020 | 102-1 v Matlock TownGainsborough Trinity 2-1 Matlock Town | BetVictor Northern Premier Division |
| 6 | Sat 4 Jan 2020 | 102-2 v Whitby TownWhitby Town 2-2 Gainsborough Trinity | BetVictor Northern Premier Division |
| 7 | Sat 18 Jan 2020 | 112-0 v RadcliffeRadcliffe 0-2 Gainsborough Trinity | BetVictor Northern Premier Division |
| 8 | Sat 25 Jan 2020 | 73-1 v Atherton CollieriesAtherton Collieries 1-3 Gainsborough Trinity | BetVictor Northern Premier Division |
| 9 | Sat 1 Feb 2020 | 71-0 v Basford UnitedGainsborough Trinity 1-0 Basford United | BetVictor Northern Premier Division |
| 10 | Sat 15 Feb 2020 | 171-3 v Stalybridge CelticGainsborough Trinity 1-3 Stalybridge Celtic | BetVictor Northern Premier Division |
| 11 | Tue 18 Feb 2020 | 71-1 v Kidsgrove AthleticGainsborough Trinity 1-1 Kidsgrove Athletic | Integro League Cup Third Round |
| 12 | Sat 29 Feb 2020 | 71-4 v South ShieldsGainsborough Trinity 1-4 South Shields | BetVictor Northern Premier Division |
| 13 | Tue 3 Mar 2020 | 164-1 v RadcliffeGainsborough Trinity 4-1 Radcliffe | BetVictor Northern Premier Division |
| 14 | Sat 7 Mar 2020 | 171-0 v Lancaster CityLancaster City 0-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 15 | Tue 10 Mar 2020 | 172-2 v Stafford RangersStafford Rangers 2-2 Gainsborough Trinity | BetVictor Northern Premier Division |
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