| 1 | Sat 3 Aug 2019 | 2-0 v Bolton WanderersWycombe Wanderers 2-0 Bolton Wanderers | Sky Bet League One |
| 2 | Sat 10 Aug 2019 | 0-0 v Bristol RoversBristol Rovers 0-0 Wycombe Wanderers | Sky Bet League One |
| 3 | Tue 13 Aug 2019 | 1-1 v ReadingWycombe Wanderers 1-1 Reading | Carabao Cup First Round |
| 4 | Sat 17 Aug 2019 | 3-2 v Milton Keynes DonsWycombe Wanderers 3-2 Milton Keynes Dons | Sky Bet League One |
| 5 | Tue 20 Aug 2019 | 1-1 v Fleetwood TownFleetwood Town 1-1 Wycombe Wanderers | Sky Bet League One |
| 6 | Sat 24 Aug 2019 | 4-3 v Southend UnitedWycombe Wanderers 4-3 Southend United | Sky Bet League One |
| 7 | Sat 31 Aug 2019 | 0-0 v AFC WimbledonAFC Wimbledon 0-0 Wycombe Wanderers | Sky Bet League One |
| 8 | Sat 14 Sep 2019 | 0-2 v GillinghamGillingham 2-0 Wycombe Wanderers | Sky Bet League One |
| 9 | Sat 21 Sep 2019 | 1-0 v PortsmouthWycombe Wanderers 1-0 Portsmouth | Sky Bet League One |
| 10 | Sat 28 Sep 2019 | 3-0 v RochdaleRochdale 0-3 Wycombe Wanderers | Sky Bet League One |
| 11 | Sat 19 Oct 2019 | 1-0 v SunderlandWycombe Wanderers 1-0 Sunderland | Sky Bet League One |
| 12 | Sat 26 Oct 2019 | 1-0 v Rotherham UnitedRotherham United 0-1 Wycombe Wanderers | Sky Bet League One |
| 13 | Sat 2 Nov 2019 | 1-0 v Shrewsbury TownWycombe Wanderers 1-0 Shrewsbury Town | Sky Bet League One |
| 14 | Tue 12 Nov 2019 | 2-1 v Milton Keynes DonsMilton Keynes Dons 1-2 Wycombe Wanderers | Leasing.com Trophy Southern Group G |
| 15 | Wed 20 Nov 2019 | 1-2 v Tranmere RoversWycombe Wanderers 1-2 Tranmere Rovers | Emirates FA Cup First Round Replay |
| 16 | Sat 14 Dec 2019 | 2-0 v Burton AlbionWycombe Wanderers 2-0 Burton Albion | Sky Bet League One |
| 17 | Thu 26 Dec 2019 | 0-2 v PortsmouthPortsmouth 2-0 Wycombe Wanderers | Sky Bet League One |
| 18 | Sat 11 Jan 2020 | 0-4 v SunderlandSunderland 4-0 Wycombe Wanderers | Sky Bet League One |
| 19 | Sat 1 Feb 2020 | 0-2 v Milton Keynes DonsMilton Keynes Dons 2-0 Wycombe Wanderers | Sky Bet League One |
| 20 | Tue 11 Feb 2020 | 0-1 v Fleetwood TownWycombe Wanderers 0-1 Fleetwood Town | Sky Bet League One |
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