1 | Tue 13 Aug 2019 | 2-2 v Crewe AlexandraMiddlesbrough 2-2 Crewe Alexandra | Carabao Cup First Round |
2 | Wed 23 Oct 2019 | 0-0 v Huddersfield TownHuddersfield Town 0-0 Middlesbrough | Sky Bet Championship |
3 | Sat 26 Oct 2019 | 0-0 v FulhamMiddlesbrough 0-0 Fulham | Sky Bet Championship |
4 | Sat 2 Nov 2019 | 0-2 v Derby CountyDerby County 2-0 Middlesbrough | Sky Bet Championship |
5 | Wed 27 Nov 2019 | 1-0 v BarnsleyMiddlesbrough 1-0 Barnsley | Sky Bet Championship |
6 | Sat 30 Nov 2019 | 0-4 v Leeds UnitedLeeds United 4-0 Middlesbrough | Sky Bet Championship |
7 | Sat 7 Dec 2019 | 1-0 v Charlton AthleticMiddlesbrough 1-0 Charlton Athletic | Sky Bet Championship |
8 | Tue 10 Dec 2019 | 1-1 v Nottingham ForestNottingham Forest 1-1 Middlesbrough | Sky Bet Championship |
9 | Sat 14 Dec 2019 | 1-3 v Swansea CitySwansea City 3-1 Middlesbrough | Sky Bet Championship |
10 | Fri 20 Dec 2019 | 2-1 v Stoke CityMiddlesbrough 2-1 Stoke City | Sky Bet Championship |
11 | Thu 26 Dec 2019 | 1-0 v Huddersfield TownMiddlesbrough 1-0 Huddersfield Town | Sky Bet Championship |
12 | Sun 29 Dec 2019 | 2-0 v West Bromwich AlbionWest Bromwich Albion 0-2 Middlesbrough | Sky Bet Championship |
13 | Wed 1 Jan 2020 | 2-0 v Preston North EndPreston North End 0-2 Middlesbrough | Sky Bet Championship |
14 | Sat 11 Jan 2020 | 2-2 v Derby CountyMiddlesbrough 2-2 Derby County | Sky Bet Championship |
15 | Fri 17 Jan 2020 | 0-1 v FulhamFulham 1-0 Middlesbrough | Sky Bet Championship |
16 | Tue 21 Jan 2020 | 1-1 v Birmingham CityMiddlesbrough 1-1 Birmingham City | Sky Bet Championship |
17 | Sat 1 Feb 2020 | 1-1 v Blackburn RoversMiddlesbrough 1-1 Blackburn Rovers | Sky Bet Championship |
18 | Sat 8 Feb 2020 | 2-3 v BrentfordBrentford 3-2 Middlesbrough | Sky Bet Championship |
19 | Tue 11 Feb 2020 | 2-2 v Wigan AthleticWigan Athletic 2-2 Middlesbrough | Sky Bet Championship |
20 | Sat 15 Feb 2020 | 0-1 v Luton TownMiddlesbrough 0-1 Luton Town | Sky Bet Championship |
21 | Sat 22 Feb 2020 | 0-1 v BarnsleyBarnsley 1-0 Middlesbrough | Sky Bet Championship |
22 | Wed 26 Feb 2020 | 0-1 v Leeds UnitedMiddlesbrough 0-1 Leeds United | Sky Bet Championship |
23 | Mon 2 Mar 2020 | 2-2 v Nottingham ForestMiddlesbrough 2-2 Nottingham Forest | Sky Bet Championship |
24 | Tue 14 Jul 2020 | 422-1 v ReadingReading 1-2 Middlesbrough | Sky Bet Championship |
25 | Sat 18 Jul 2020 | 421-3 v Cardiff CityMiddlesbrough 1-3 Cardiff City | Sky Bet Championship |