| 1 | Tue 13 Aug 2019 | 1-1 v ReadingWycombe Wanderers 1-1 Reading | Carabao Cup First Round |
| 2 | Tue 20 Aug 2019 | 1-1 v Fleetwood TownFleetwood Town 1-1 Wycombe Wanderers | Sky Bet League One |
| 3 | Sat 31 Aug 2019 | 0-0 v AFC WimbledonAFC Wimbledon 0-0 Wycombe Wanderers | Sky Bet League One |
| 4 | Tue 17 Sep 2019 | 1-1 v Accrington StanleyWycombe Wanderers 1-1 Accrington Stanley | Sky Bet League One |
| 5 | Sat 28 Sep 2019 | 3-0 v RochdaleRochdale 0-3 Wycombe Wanderers | Sky Bet League One |
| 6 | Tue 8 Oct 2019 | 0-1 v StevenageWycombe Wanderers 0-1 Stevenage | Leasing.com Trophy Southern Group G |
| 7 | Sat 19 Oct 2019 | 1-0 v SunderlandWycombe Wanderers 1-0 Sunderland | Sky Bet League One |
| 8 | Tue 12 Nov 2019 | 2-1 v Milton Keynes DonsMilton Keynes Dons 1-2 Wycombe Wanderers | Leasing.com Trophy Southern Group G |
| 9 | Sun 29 Dec 2019 | 1-4 v Coventry CityWycombe Wanderers 1-4 Coventry City | Sky Bet League One |
| 10 | Sat 11 Jan 2020 | 0-4 v SunderlandSunderland 4-0 Wycombe Wanderers | Sky Bet League One |
| 11 | Tue 21 Jan 2020 | 0-4 v Peterborough UnitedPeterborough United 4-0 Wycombe Wanderers | Sky Bet League One |
| 12 | Sat 1 Feb 2020 | 0-2 v Milton Keynes DonsMilton Keynes Dons 2-0 Wycombe Wanderers | Sky Bet League One |
| 13 | Tue 11 Feb 2020 | 0-1 v Fleetwood TownWycombe Wanderers 0-1 Fleetwood Town | Sky Bet League One |
| 14 | Sat 15 Feb 2020 | 2-0 v Bolton WanderersBolton Wanderers 0-2 Wycombe Wanderers | Sky Bet League One |
| 15 | Sat 29 Feb 2020 | 1-3 v Doncaster RoversDoncaster Rovers 3-1 Wycombe Wanderers | Sky Bet League One |
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