| 1 | Sun 11 Aug 2019 | 0-0 v Leicester CityLeicester City 0-0 Wolverhampton Wanderers | Premier League |
| 2 | Thu 15 Aug 2019 | 4-0 v PyunikWolverhampton Wanderers 4-0 Pyunik | Europa League Third Qualifying Round |
| 3 | Mon 19 Aug 2019 | 1-1 v Manchester UnitedWolverhampton Wanderers 1-1 Manchester United | Premier League |
| 4 | Sun 1 Sep 2019 | 2-3 v EvertonEverton 3-2 Wolverhampton Wanderers | Premier League |
| 5 | Sat 14 Sep 2019 | 2-5 v ChelseaWolverhampton Wanderers 2-5 Chelsea | Premier League |
| 6 | Thu 19 Sep 2019 | 0-1 v Sporting BragaWolverhampton Wanderers 0-1 Sporting Braga | Europa League Group K |
| 7 | Sun 22 Sep 2019 | 1-1 v Crystal PalaceCrystal Palace 1-1 Wolverhampton Wanderers | Premier League |
| 8 | Wed 25 Sep 2019 | 1-1 v ReadingWolverhampton Wanderers 1-1 Reading | Carabao Cup Third Round |
| 9 | Sat 28 Sep 2019 | 2-0 v WatfordWolverhampton Wanderers 2-0 Watford | Premier League |
| 10 | Thu 3 Oct 2019 | 1-0 v BeşiktaşBeşiktaş 0-1 Wolverhampton Wanderers | Europa League Group K |
| 11 | Sun 6 Oct 2019 | 2-0 v Manchester CityManchester City 0-2 Wolverhampton Wanderers | Premier League |
| 12 | Sat 19 Oct 2019 | 1-1 v SouthamptonWolverhampton Wanderers 1-1 Southampton | Premier League |
| 13 | Thu 24 Oct 2019 | 2-1 v Slovan BratislavaSlovan Bratislava 1-2 Wolverhampton Wanderers | Europa League Group K |
| 14 | Thu 7 Nov 2019 | 1-0 v Slovan BratislavaWolverhampton Wanderers 1-0 Slovan Bratislava | Europa League Group K |
| 15 | Sun 10 Nov 2019 | 2-1 v Aston VillaWolverhampton Wanderers 2-1 Aston Villa | Premier League |
| 16 | Thu 28 Nov 2019 | 3-3 v Sporting BragaSporting Braga 3-3 Wolverhampton Wanderers | Europa League Group K |
| 17 | Wed 4 Dec 2019 | 2-0 v West Ham UnitedWolverhampton Wanderers 2-0 West Ham United | Premier League |
| 18 | Sun 8 Dec 2019 | 2-2 v Brighton & Hove AlbionBrighton & Hove Albion 2-2 Wolverhampton Wanderers | Premier League |
| 19 | Sat 21 Dec 2019 | 2-1 v Norwich CityNorwich City 1-2 Wolverhampton Wanderers | Premier League |
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