| 1 | 5/9/2020 | 10-5 v Cleethorpes TownCleethorpes Town 5-0 Gainsborough Trinity | Friendly |
| 2 | 19/9/2020 | 12-0 v Hyde UnitedGainsborough Trinity 2-0 Hyde United | Northern Premier League - Premier Division |
| 3 | 22/9/2020 | 10-3 v AFC MansfieldAFC Mansfield 3-0 Gainsborough Trinity | Emirates FA Cup First Qualifying Round |
| 4 | 26/9/2020 | 10-3 v Warrington TownWarrington Town 3-0 Gainsborough Trinity | Northern Premier League - Premier Division |
| 5 | 29/9/2020 | 15-1 v Whitby TownGainsborough Trinity 5-1 Whitby Town | Northern Premier League - Premier Division |
| 6 | 17/10/2020 | 11-3 v Witton AlbionGainsborough Trinity 1-3 Witton Albion | Northern Premier League - Premier Division |
| 7 | 20/10/2020 | 1 3-2 v Stalybridge CelticGainsborough Trinity 3-2 Stalybridge Celtic | Northern Premier League - Premier Division |
| 8 | 24/10/2020 | 11-2 v RadcliffeRadcliffe 2-1 Gainsborough Trinity | Northern Premier League - Premier Division |
| 9 | 27/10/2020 | 11-0 v Bamber BridgeBamber Bridge 0-1 Gainsborough Trinity | Northern Premier League - Premier Division |
| 10 | 31/10/2020 | 12-4 v Peterborough SportsPeterborough Sports 4-2 Gainsborough Trinity | Buildbase FA Trophy Third Qualifying Round |
| 11 | 3/11/2020 | 10-1 v South ShieldsGainsborough Trinity 0-1 South Shields | Northern Premier League - Premier Division |
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