| 1 | Sat 10 Aug 2019 | 11-0 v Prescot CablesPrescot Cables 0-1 Market Drayton Town | Friendly |
| 2 | Sat 17 Aug 2019 | 13-4 v Belper TownMarket Drayton Town 3-4 Belper Town | BetVictor Northern South East Division |
| 3 | Tue 20 Aug 2019 | 11-2 v ChasetownChasetown 2-1 Market Drayton Town | BetVictor Northern South East Division |
| 4 | Sat 31 Aug 2019 | 11-0 v Spalding UnitedSpalding United 0-1 Market Drayton Town | BetVictor Northern South East Division |
| 5 | Tue 3 Sep 2019 | 11-2 v Leek TownMarket Drayton Town 1-2 Leek Town | BetVictor Northern South East Division |
| 6 | Sat 7 Sep 2019 | 12-3 v Lincoln UnitedMarket Drayton Town 2-3 Lincoln United | BetVictor Northern South East Division |
| 7 | Tue 10 Sep 2019 | 10-2 v Kidsgrove AthleticMarket Drayton Town 0-2 Kidsgrove Athletic | BetVictor Northern South East Division |
| 8 | Sat 14 Sep 2019 | 10-3 v IlkestonIlkeston 3-0 Market Drayton Town | BetVictor Northern South East Division |
| 9 | Sat 21 Sep 2019 | 10-2 v Frickley AthleticMarket Drayton Town 0-2 Frickley Athletic | BetVictor Northern South East Division |
| 10 | Tue 24 Sep 2019 | 10-7 v Loughborough DynamoLoughborough Dynamo 7-0 Market Drayton Town | BetVictor Northern South East Division |
| 11 | Sat 28 Sep 2019 | 10-2 v Sutton Coldfield TownSutton Coldfield Town 2-0 Market Drayton Town | BetVictor Northern South East Division |
| 12 | Sun 13 Oct 2019 | 11-2 v Cambridge CityCambridge City 2-1 Market Drayton Town | Buildbase FA Trophy Preliminary Round |
| 13 | Sat 2 Nov 2019 | 12-1 v Wisbech TownMarket Drayton Town 2-1 Wisbech Town | BetVictor Northern South East Division |
| 14 | Tue 3 Dec 2019 | 12-0 v Sutton Coldfield TownMarket Drayton Town 2-0 Sutton Coldfield Town | Integro League Cup First Round |
| 15 | Sat 7 Dec 2019 | 11-4 v Frickley AthleticFrickley Athletic 4-1 Market Drayton Town | BetVictor Northern South East Division |
| 16 | Mon 9 Dec 2019 | 11-2 v Kidsgrove AthleticKidsgrove Athletic 2-1 Market Drayton Town | Integro League Cup Second Round |
| 17 | Sat 21 Dec 2019 | 12-5 v Belper TownBelper Town 5-2 Market Drayton Town | BetVictor Northern South East Division |
| 18 | Wed 1 Jan 2020 | 13-2 v Newcastle TownNewcastle Town 2-3 Market Drayton Town | BetVictor Northern South East Division |
| 19 | Sat 8 Feb 2020 | 10-1 v Stocksbridge Park SteelsMarket Drayton Town 0-1 Stocksbridge Park Steels | BetVictor Northern South East Division |
| 20 | Sat 14 Mar 2020 | 14-0 v Wisbech TownWisbech Town 0-4 Market Drayton Town | BetVictor Northern South East Division |
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