| 1 | Sat 3 Aug 2019 | 2-0 v Bolton WanderersWycombe Wanderers 2-0 Bolton Wanderers | Sky Bet League One |
| 2 | Tue 13 Aug 2019 | 1-1 v ReadingWycombe Wanderers 1-1 Reading | Carabao Cup First Round |
| 3 | Sat 17 Aug 2019 | 3-2 v Milton Keynes DonsWycombe Wanderers 3-2 Milton Keynes Dons | Sky Bet League One |
| 4 | Tue 20 Aug 2019 | 1-1 v Fleetwood TownFleetwood Town 1-1 Wycombe Wanderers | Sky Bet League One |
| 5 | Sat 24 Aug 2019 | 4-3 v Southend UnitedWycombe Wanderers 4-3 Southend United | Sky Bet League One |
| 6 | Sat 31 Aug 2019 | 0-0 v AFC WimbledonAFC Wimbledon 0-0 Wycombe Wanderers | Sky Bet League One |
| 7 | Sat 7 Sep 2019 | 3-1 v Lincoln CityWycombe Wanderers 3-1 Lincoln City | Sky Bet League One |
| 8 | Sat 14 Sep 2019 | 0-2 v GillinghamGillingham 2-0 Wycombe Wanderers | Sky Bet League One |
| 9 | Tue 17 Sep 2019 | 1-1 v Accrington StanleyWycombe Wanderers 1-1 Accrington Stanley | Sky Bet League One |
| 10 | Sat 28 Sep 2019 | 3-0 v RochdaleRochdale 0-3 Wycombe Wanderers | Sky Bet League One |
| 11 | Sat 5 Oct 2019 | 3-3 v Peterborough UnitedWycombe Wanderers 3-3 Peterborough United | Sky Bet League One |
| 12 | Sat 19 Oct 2019 | 1-0 v SunderlandWycombe Wanderers 1-0 Sunderland | Sky Bet League One |
| 13 | Tue 22 Oct 2019 | 1-1 v BlackpoolBlackpool 1-1 Wycombe Wanderers | Sky Bet League One |
| 14 | Sat 26 Oct 2019 | 1-0 v Rotherham UnitedRotherham United 0-1 Wycombe Wanderers | Sky Bet League One |
| 15 | Sat 2 Nov 2019 | 1-0 v Shrewsbury TownWycombe Wanderers 1-0 Shrewsbury Town | Sky Bet League One |
| 16 | Sat 9 Nov 2019 | 2-2 v Tranmere RoversTranmere Rovers 2-2 Wycombe Wanderers | Emirates FA Cup First Round |
| 17 | Sun 17 Nov 2019 | 2-0 v Tranmere RoversTranmere Rovers 0-2 Wycombe Wanderers | Sky Bet League One |
| 18 | Wed 20 Nov 2019 | 1-2 v Tranmere RoversWycombe Wanderers 1-2 Tranmere Rovers | Emirates FA Cup First Round Replay |
| 19 | Sat 23 Nov 2019 | 1-0 v Doncaster RoversWycombe Wanderers 1-0 Doncaster Rovers | Sky Bet League One |
| 20 | Sat 14 Dec 2019 | 2-0 v Burton AlbionWycombe Wanderers 2-0 Burton Albion | Sky Bet League One |
| 21 | Sat 21 Dec 2019 | 0-1 v Oxford UnitedOxford United 1-0 Wycombe Wanderers | Sky Bet League One |
| 22 | Thu 26 Dec 2019 | 0-2 v PortsmouthPortsmouth 2-0 Wycombe Wanderers | Sky Bet League One |
| 23 | Sun 29 Dec 2019 | 1-4 v Coventry CityWycombe Wanderers 1-4 Coventry City | Sky Bet League One |
| 24 | Wed 1 Jan 2020 | 1-1 v Ipswich TownWycombe Wanderers 1-1 Ipswich Town | Sky Bet League One |
| 25 | Sat 11 Jan 2020 | 0-4 v SunderlandSunderland 4-0 Wycombe Wanderers | Sky Bet League One |
| 26 | Sat 1 Feb 2020 | 0-2 v Milton Keynes DonsMilton Keynes Dons 2-0 Wycombe Wanderers | Sky Bet League One |
| 27 | Sat 8 Feb 2020 | 3-1 v Bristol RoversWycombe Wanderers 3-1 Bristol Rovers | Sky Bet League One |
| 28 | Tue 11 Feb 2020 | 0-1 v Fleetwood TownWycombe Wanderers 0-1 Fleetwood Town | Sky Bet League One |
| 29 | Sat 15 Feb 2020 | 2-0 v Bolton WanderersBolton Wanderers 0-2 Wycombe Wanderers | Sky Bet League One |
| 30 | Sat 22 Feb 2020 | 3-1 v Tranmere RoversWycombe Wanderers 3-1 Tranmere Rovers | Sky Bet League One |
| 31 | Sat 29 Feb 2020 | 1-3 v Doncaster RoversDoncaster Rovers 3-1 Wycombe Wanderers | Sky Bet League One |
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