| 1 | 3/8/2019 | 2-0 v Bolton WanderersWycombe Wanderers 2-0 Bolton Wanderers | Sky Bet League One |
| 2 | 10/8/2019 | 0-0 v Bristol RoversBristol Rovers 0-0 Wycombe Wanderers | Sky Bet League One |
| 3 | 13/8/2019 | 1-1 v ReadingWycombe Wanderers 1-1 Reading | Carabao Cup First Round |
| 4 | 17/8/2019 | 3-2 v Milton Keynes DonsWycombe Wanderers 3-2 Milton Keynes Dons | Sky Bet League One |
| 5 | 20/8/2019 | 1-1 v Fleetwood TownFleetwood Town 1-1 Wycombe Wanderers | Sky Bet League One |
| 6 | 24/8/2019 | 4-3 v Southend UnitedWycombe Wanderers 4-3 Southend United | Sky Bet League One |
| 7 | 31/8/2019 | 0-0 v AFC WimbledonAFC Wimbledon 0-0 Wycombe Wanderers | Sky Bet League One |
| 8 | 7/9/2019 | 3-1 v Lincoln CityWycombe Wanderers 3-1 Lincoln City | Sky Bet League One |
| 9 | 14/9/2019 | 0-2 v GillinghamGillingham 2-0 Wycombe Wanderers | Sky Bet League One |
| 10 | 17/9/2019 | 1-1 v Accrington StanleyWycombe Wanderers 1-1 Accrington Stanley | Sky Bet League One |
| 11 | 21/9/2019 | 1-0 v PortsmouthWycombe Wanderers 1-0 Portsmouth | Sky Bet League One |
| 12 | 28/9/2019 | 3-0 v RochdaleRochdale 0-3 Wycombe Wanderers | Sky Bet League One |
| 13 | 5/10/2019 | 3-3 v Peterborough UnitedWycombe Wanderers 3-3 Peterborough United | Sky Bet League One |
| 14 | 8/10/2019 | 0-1 v StevenageWycombe Wanderers 0-1 Stevenage | Checkatrade Trophy Southern Group G |
| 15 | 19/10/2019 | 1-0 v SunderlandWycombe Wanderers 1-0 Sunderland | Sky Bet League One |
| 16 | 22/10/2019 | 1-1 v BlackpoolBlackpool 1-1 Wycombe Wanderers | Sky Bet League One |
| 17 | 26/10/2019 | 1-0 v Rotherham UnitedRotherham United 0-1 Wycombe Wanderers | Sky Bet League One |
| 18 | 2/11/2019 | 1-0 v Shrewsbury TownWycombe Wanderers 1-0 Shrewsbury Town | Sky Bet League One |
| 19 | 9/11/2019 | 2-2 v Tranmere RoversTranmere Rovers 2-2 Wycombe Wanderers | Emirates FA Cup First Round |
| 20 | 12/11/2019 | 2-1 v Milton Keynes DonsMilton Keynes Dons 1-2 Wycombe Wanderers | Checkatrade Trophy Southern Group G |
| 21 | 17/11/2019 | 2-0 v Tranmere RoversTranmere Rovers 0-2 Wycombe Wanderers | Sky Bet League One |
| 22 | 20/11/2019 | 1-2 v Tranmere RoversWycombe Wanderers 1-2 Tranmere Rovers | Emirates FA Cup First Round Replay |
| 23 | 23/11/2019 | 1-0 v Doncaster RoversWycombe Wanderers 1-0 Doncaster Rovers | Sky Bet League One |
