| 1 | Sat 23 Nov 2019 | 6 1-0 v Glossop North EndGlossop North End 0-1 Market Drayton Town | BetVictor Northern South East Division |
| 2 | Tue 3 Dec 2019 | 152-0 v Sutton Coldfield TownMarket Drayton Town 2-0 Sutton Coldfield Town | Integro League Cup First Round |
| 3 | Sat 7 Dec 2019 | 6 1-4 v Frickley AthleticFrickley Athletic 4-1 Market Drayton Town | BetVictor Northern South East Division |
| 4 | Mon 9 Dec 2019 | 61-2 v Kidsgrove AthleticKidsgrove Athletic 2-1 Market Drayton Town | Integro League Cup Second Round |
| 5 | Sat 21 Dec 2019 | 82-5 v Belper TownBelper Town 5-2 Market Drayton Town | BetVictor Northern South East Division |
| 6 | Sat 28 Dec 2019 | 72-9 v Cleethorpes TownMarket Drayton Town 2-9 Cleethorpes Town | BetVictor Northern South East Division |
| 7 | Wed 1 Jan 2020 | 83-2 v Newcastle TownNewcastle Town 2-3 Market Drayton Town | BetVictor Northern South East Division |
| 8 | Sat 4 Jan 2020 | 80-1 v ChasetownMarket Drayton Town 0-1 Chasetown | BetVictor Northern South East Division |
| 9 | Sat 11 Jan 2020 | 81-4 v Leek TownLeek Town 4-1 Market Drayton Town | BetVictor Northern South East Division |
| 10 | Sat 18 Jan 2020 | 81-3 v Worksop TownWorksop Town 3-1 Market Drayton Town | BetVictor Northern South East Division |
| 11 | Sat 8 Feb 2020 | 160-1 v Stocksbridge Park SteelsMarket Drayton Town 0-1 Stocksbridge Park Steels | BetVictor Northern South East Division |
| 12 | Sat 7 Mar 2020 | 100-1 v IlkestonMarket Drayton Town 0-1 Ilkeston | BetVictor Northern South East Division |
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