| 1 | Sat 17 Aug 2019 | 111-2 v Nantwich TownNantwich Town 2-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 2 | Sat 24 Aug 2019 | 110-0 v Warrington TownGainsborough Trinity 0-0 Warrington Town | BetVictor Northern Premier Division |
| 3 | Mon 26 Aug 2019 | 111-2 v Matlock TownMatlock Town 2-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 4 | Sat 31 Aug 2019 | 72-4 v Lancaster CityGainsborough Trinity 2-4 Lancaster City | BetVictor Northern Premier Division |
| 5 | Sat 7 Sep 2019 | 102-2 v Banbury UnitedBanbury United 2-2 Gainsborough Trinity | Emirates FA Cup First Qualifying Round |
| 6 | Tue 10 Sep 2019 | 71-0 v Banbury UnitedGainsborough Trinity 1-0 Banbury United | Emirates FA Cup First Qualifying Round Replay |
| 7 | Sat 14 Sep 2019 | 70-1 v Witton AlbionWitton Albion 1-0 Gainsborough Trinity | BetVictor Northern Premier Division |
| 8 | Sat 21 Sep 2019 | 70-2 v Rushall OlympicRushall Olympic 2-0 Gainsborough Trinity | Emirates FA Cup Second Qualifying Round |
| 9 | Tue 24 Sep 2019 | 80-2 v South ShieldsSouth Shields 2-0 Gainsborough Trinity | BetVictor Northern Premier Division |
| 10 | Sat 28 Sep 2019 | 82-2 v Mickleover SportsGainsborough Trinity 2-2 Mickleover Sports | BetVictor Northern Premier Division |
| 11 | Tue 1 Oct 2019 | 84-1 v Bamber BridgeGainsborough Trinity 4-1 Bamber Bridge | BetVictor Northern Premier Division |
| 12 | Sat 5 Oct 2019 | 8 3-4 v Basford UnitedBasford United 4-3 Gainsborough Trinity | BetVictor Northern Premier Division |
| 13 | Sat 12 Oct 2019 | 110-2 v Atherton CollieriesGainsborough Trinity 0-2 Atherton Collieries | BetVictor Northern Premier Division |
| 14 | Tue 15 Oct 2019 | 20-0 v BuxtonGainsborough Trinity 0-0 Buxton | BetVictor Northern Premier Division |
| 15 | Sat 19 Oct 2019 | 41-3 v Ashton UnitedAshton United 3-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 16 | Tue 29 Oct 2019 | 84-0 v DunstonDunston 0-4 Gainsborough Trinity | Buildbase FA Trophy First Qualifying Round |
| 17 | Sat 2 Nov 2019 | 22-2 v FC United of ManchesterFC United of Manchester 2-2 Gainsborough Trinity | BetVictor Northern Premier Division |
| 18 | Sat 9 Nov 2019 | 25-3 v TamworthTamworth 3-5 Gainsborough Trinity | Buildbase FA Trophy Second Qualifying Round |
| 19 | Sat 16 Nov 2019 | 20-1 v Morpeth TownGainsborough Trinity 0-1 Morpeth Town | BetVictor Northern Premier Division |
| 20 | Sat 7 Dec 2019 | 22-3 v Scarborough AthleticGainsborough Trinity 2-3 Scarborough Athletic | BetVictor Northern Premier Division |
| 21 | Sat 14 Dec 2019 | 21-1 v Hyde UnitedHyde United 1-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 22 | Sat 4 Jan 2020 | 72-2 v Whitby TownWhitby Town 2-2 Gainsborough Trinity | BetVictor Northern Premier Division |
| 23 | Sat 18 Jan 2020 | 42-0 v RadcliffeRadcliffe 0-2 Gainsborough Trinity | BetVictor Northern Premier Division |
| 24 | Sat 25 Jan 2020 | 43-1 v Atherton CollieriesAtherton Collieries 1-3 Gainsborough Trinity | BetVictor Northern Premier Division |
| 25 | Sat 1 Feb 2020 | 41-0 v Basford UnitedGainsborough Trinity 1-0 Basford United | BetVictor Northern Premier Division |
| 26 | Tue 4 Feb 2020 | 42-1 v Stalybridge CelticStalybridge Celtic 1-2 Gainsborough Trinity | BetVictor Northern Premier Division |
| 27 | Sat 8 Feb 2020 | 4 3-3 v BuxtonBuxton 3-3 Gainsborough Trinity | BetVictor Northern Premier Division |
| 28 | Sat 15 Feb 2020 | 141-3 v Stalybridge CelticGainsborough Trinity 1-3 Stalybridge Celtic | BetVictor Northern Premier Division |
| 29 | Tue 18 Feb 2020 | 81-1 v Kidsgrove AthleticGainsborough Trinity 1-1 Kidsgrove Athletic | Integro League Cup Third Round |
| 30 | Sat 29 Feb 2020 | 41-4 v South ShieldsGainsborough Trinity 1-4 South Shields | BetVictor Northern Premier Division |
| 31 | Tue 3 Mar 2020 | 8 4-1 v RadcliffeGainsborough Trinity 4-1 Radcliffe | BetVictor Northern Premier Division |
| 32 | Sat 7 Mar 2020 | 81-0 v Lancaster CityLancaster City 0-1 Gainsborough Trinity | BetVictor Northern Premier Division |
| 33 | Tue 10 Mar 2020 | 82-2 v Stafford RangersStafford Rangers 2-2 Gainsborough Trinity | BetVictor Northern Premier Division |
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