| 1 | Tue 24 Sep 2019 | 10-2 v South ShieldsSouth Shields 2-0 Gainsborough Trinity | BetVictor Northern Premier Division |
| 2 | Sat 28 Sep 2019 | 12-2 v Mickleover SportsGainsborough Trinity 2-2 Mickleover Sports | BetVictor Northern Premier Division |
| 3 | Tue 1 Oct 2019 | 14-1 v Bamber BridgeGainsborough Trinity 4-1 Bamber Bridge | BetVictor Northern Premier Division |
| 4 | Sat 5 Oct 2019 | 13-4 v Basford UnitedBasford United 4-3 Gainsborough Trinity | BetVictor Northern Premier Division |
| 5 | Sat 12 Oct 2019 | 10-2 v Atherton CollieriesGainsborough Trinity 0-2 Atherton Collieries | BetVictor Northern Premier Division |
| 6 | Tue 15 Oct 2019 | 10-0 v BuxtonGainsborough Trinity 0-0 Buxton | BetVictor Northern Premier Division |
| 7 | Sat 1 Feb 2020 | 11-0 v Basford UnitedGainsborough Trinity 1-0 Basford United | BetVictor Northern Premier Division |
| 8 | Tue 4 Feb 2020 | 12-1 v Stalybridge CelticStalybridge Celtic 1-2 Gainsborough Trinity | BetVictor Northern Premier Division |
| 9 | Sat 8 Feb 2020 | 13-3 v BuxtonBuxton 3-3 Gainsborough Trinity | BetVictor Northern Premier Division |
| 10 | Sat 15 Feb 2020 | 11-3 v Stalybridge CelticGainsborough Trinity 1-3 Stalybridge Celtic | BetVictor Northern Premier Division |
| 11 | Tue 18 Feb 2020 | 11-1 v Kidsgrove AthleticGainsborough Trinity 1-1 Kidsgrove Athletic | Integro League Cup Third Round |
| 12 | Sat 29 Feb 2020 | 11-4 v South ShieldsGainsborough Trinity 1-4 South Shields | BetVictor Northern Premier Division |
| 13 | Tue 3 Mar 2020 | 1 4-1 v RadcliffeGainsborough Trinity 4-1 Radcliffe | BetVictor Northern Premier Division |
| 14 | Sat 7 Mar 2020 | 11-0 v Lancaster CityLancaster City 0-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 15 | Tue 10 Mar 2020 | 12-2 v Stafford RangersStafford Rangers 2-2 Gainsborough Trinity | BetVictor Northern Premier Division |
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