| 1 | Sat 10 Aug 2019 | 101-0 v Prescot CablesPrescot Cables 0-1 Market Drayton Town | Friendly |
| 2 | Sat 17 Aug 2019 | 103-4 v Belper TownMarket Drayton Town 3-4 Belper Town | BetVictor Northern South East Division |
| 3 | Tue 20 Aug 2019 | 101-2 v ChasetownChasetown 2-1 Market Drayton Town | BetVictor Northern South East Division |
| 4 | Mon 26 Aug 2019 | 92-5 v Newcastle TownMarket Drayton Town 2-5 Newcastle Town | BetVictor Northern South East Division |
| 5 | Sat 31 Aug 2019 | 101-0 v Spalding UnitedSpalding United 0-1 Market Drayton Town | BetVictor Northern South East Division |
| 6 | Sat 7 Sep 2019 | 10 2-3 v Lincoln UnitedMarket Drayton Town 2-3 Lincoln United | BetVictor Northern South East Division |
| 7 | Tue 10 Sep 2019 | 40-2 v Kidsgrove AthleticMarket Drayton Town 0-2 Kidsgrove Athletic | BetVictor Northern South East Division |
| 8 | Sat 21 Sep 2019 | 90-2 v Frickley AthleticMarket Drayton Town 0-2 Frickley Athletic | BetVictor Northern South East Division |
| 9 | Sat 28 Sep 2019 | 90-2 v Sutton Coldfield TownSutton Coldfield Town 2-0 Market Drayton Town | BetVictor Northern South East Division |
| 10 | Sat 5 Oct 2019 | 10 1-4 v Worksop TownMarket Drayton Town 1-4 Worksop Town | BetVictor Northern South East Division |
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