| 1 | Sat 17 Aug 2019 | 2-1 v 1. FC KölnVfL Wolfsburg 2-1 1. FC Köln | German Bundesliga |
| 2 | Thu 19 Sep 2019 | 3-1 v OleksandriyaVfL Wolfsburg 3-1 Oleksandriya | Europa League Group I |
| 3 | Mon 23 Sep 2019 | 1-1 v 1899 HoffenheimVfL Wolfsburg 1-1 1899 Hoffenheim | German Bundesliga |
| 4 | Thu 3 Oct 2019 | 1-1 v Saint ÉtienneSaint Étienne 1-1 VfL Wolfsburg | Europa League Group I |
| 5 | Sat 19 Oct 2019 | 1-1 v RB LeipzigRB Leipzig 1-1 VfL Wolfsburg | German Bundesliga |
| 6 | Thu 24 Oct 2019 | 2-2 v KAA GentKAA Gent 2-2 VfL Wolfsburg | Europa League Group I |
| 7 | Sat 2 Nov 2019 | 0-3 v Borussia DortmundBorussia Dortmund 3-0 VfL Wolfsburg | German Bundesliga |
| 8 | Thu 7 Nov 2019 | 1-3 v KAA GentVfL Wolfsburg 1-3 KAA Gent | Europa League Group I |
| 9 | Sun 10 Nov 2019 | 0-2 v Bayer 04 LeverkusenVfL Wolfsburg 0-2 Bayer 04 Leverkusen | German Bundesliga |
| 10 | Thu 12 Dec 2019 | 1-0 v Saint ÉtienneVfL Wolfsburg 1-0 Saint Étienne | Europa League Group I |
| 11 | Sat 11 Jan 2020 | 2-2 v Derby CountyMiddlesbrough 2-2 Derby County | Sky Bet Championship |
| 12 | Tue 14 Jan 2020 | 1-2 v Tottenham HotspurTottenham Hotspur 2-1 Middlesbrough | Emirates FA Cup Third Round Replay |
| 13 | Fri 17 Jan 2020 | 0-1 v FulhamFulham 1-0 Middlesbrough | Sky Bet Championship |
| 14 | Tue 21 Jan 2020 | 1-1 v Birmingham CityMiddlesbrough 1-1 Birmingham City | Sky Bet Championship |
| 15 | Sat 1 Feb 2020 | 1-1 v Blackburn RoversMiddlesbrough 1-1 Blackburn Rovers | Sky Bet Championship |
| 16 | Sat 8 Feb 2020 | 2-3 v BrentfordBrentford 3-2 Middlesbrough | Sky Bet Championship |
| 17 | Tue 11 Feb 2020 | 2-2 v Wigan AthleticWigan Athletic 2-2 Middlesbrough | Sky Bet Championship |
| 18 | Sat 15 Feb 2020 | 0-1 v Luton TownMiddlesbrough 0-1 Luton Town | Sky Bet Championship |
| 19 | Wed 26 Feb 2020 | 0-1 v Leeds UnitedMiddlesbrough 0-1 Leeds United | Sky Bet Championship |
| 20 | Sat 20 Jun 2020 | 20 0-3 v Swansea CityMiddlesbrough 0-3 Swansea City | Sky Bet Championship |
| 21 | Sun 5 Jul 2020 | 200-1 v Queens Park RangersMiddlesbrough 0-1 Queens Park Rangers | Sky Bet Championship |
| 22 | Sat 18 Jul 2020 | 201-3 v Cardiff CityMiddlesbrough 1-3 Cardiff City | Sky Bet Championship |
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