| 1 | Sat 7 Dec 2019 | 82-3 v Scarborough AthleticGainsborough Trinity 2-3 Scarborough Athletic | BetVictor Northern Premier Division |
| 2 | Sat 14 Dec 2019 | 81-1 v Hyde UnitedHyde United 1-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 3 | Thu 26 Dec 2019 | 165-1 v Grantham TownGrantham Town 1-5 Gainsborough Trinity | BetVictor Northern Premier Division |
| 4 | Wed 1 Jan 2020 | 72-1 v Matlock TownGainsborough Trinity 2-1 Matlock Town | BetVictor Northern Premier Division |
| 5 | Sat 4 Jan 2020 | 82-2 v Whitby TownWhitby Town 2-2 Gainsborough Trinity | BetVictor Northern Premier Division |
| 6 | Sat 18 Jan 2020 | 15 2-0 v RadcliffeRadcliffe 0-2 Gainsborough Trinity | BetVictor Northern Premier Division |
| 7 | Sat 25 Jan 2020 | 83-1 v Atherton CollieriesAtherton Collieries 1-3 Gainsborough Trinity | BetVictor Northern Premier Division |
| 8 | Sat 1 Feb 2020 | 81-0 v Basford UnitedGainsborough Trinity 1-0 Basford United | BetVictor Northern Premier Division |
| 9 | Tue 4 Feb 2020 | 82-1 v Stalybridge CelticStalybridge Celtic 1-2 Gainsborough Trinity | BetVictor Northern Premier Division |
| 10 | Sat 8 Feb 2020 | 8 3-3 v BuxtonBuxton 3-3 Gainsborough Trinity | BetVictor Northern Premier Division |
| 11 | Sat 15 Feb 2020 | 81-3 v Stalybridge CelticGainsborough Trinity 1-3 Stalybridge Celtic | BetVictor Northern Premier Division |
| 12 | Tue 18 Feb 2020 | 141-1 v Kidsgrove AthleticGainsborough Trinity 1-1 Kidsgrove Athletic | Integro League Cup Third Round |
| 13 | Sat 29 Feb 2020 | 141-4 v South ShieldsGainsborough Trinity 1-4 South Shields | BetVictor Northern Premier Division |
| 14 | Tue 3 Mar 2020 | 24-1 v RadcliffeGainsborough Trinity 4-1 Radcliffe | BetVictor Northern Premier Division |
| 15 | Sat 7 Mar 2020 | 2 1-0 v Lancaster CityLancaster City 0-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 16 | Tue 10 Mar 2020 | 22-2 v Stafford RangersStafford Rangers 2-2 Gainsborough Trinity | BetVictor Northern Premier Division |
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