| 1 | Sun 13 Oct 2019 | 4 1-2 v Cambridge CityCambridge City 2-1 Market Drayton Town | Buildbase FA Trophy Preliminary Round |
| 2 | Sat 19 Oct 2019 | 44-3 v SheffieldSheffield 3-4 Market Drayton Town | BetVictor Northern South East Division |
| 3 | Sat 2 Nov 2019 | 4 2-1 v Wisbech TownMarket Drayton Town 2-1 Wisbech Town | BetVictor Northern South East Division |
| 4 | Sat 16 Nov 2019 | 40-3 v StamfordMarket Drayton Town 0-3 Stamford | BetVictor Northern South East Division |
| 5 | Sat 23 Nov 2019 | 41-0 v Glossop North EndGlossop North End 0-1 Market Drayton Town | BetVictor Northern South East Division |
| 6 | Tue 3 Dec 2019 | 122-0 v Sutton Coldfield TownMarket Drayton Town 2-0 Sutton Coldfield Town | Integro League Cup First Round |
| 7 | Sat 7 Dec 2019 | 41-4 v Frickley AthleticFrickley Athletic 4-1 Market Drayton Town | BetVictor Northern South East Division |
| 8 | Mon 9 Dec 2019 | 41-2 v Kidsgrove AthleticKidsgrove Athletic 2-1 Market Drayton Town | Integro League Cup Second Round |
| 9 | Sat 21 Dec 2019 | 42-5 v Belper TownBelper Town 5-2 Market Drayton Town | BetVictor Northern South East Division |
| 10 | Sat 28 Dec 2019 | 42-9 v Cleethorpes TownMarket Drayton Town 2-9 Cleethorpes Town | BetVictor Northern South East Division |
| 11 | Wed 1 Jan 2020 | 63-2 v Newcastle TownNewcastle Town 2-3 Market Drayton Town | BetVictor Northern South East Division |
| 12 | Sat 4 Jan 2020 | 60-1 v ChasetownMarket Drayton Town 0-1 Chasetown | BetVictor Northern South East Division |
| 13 | Sat 11 Jan 2020 | 61-4 v Leek TownLeek Town 4-1 Market Drayton Town | BetVictor Northern South East Division |
| 14 | Sat 18 Jan 2020 | 61-3 v Worksop TownWorksop Town 3-1 Market Drayton Town | BetVictor Northern South East Division |
| 15 | Sat 25 Jan 2020 | 80-6 v Sutton Coldfield TownMarket Drayton Town 0-6 Sutton Coldfield Town | BetVictor Northern South East Division |
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