| 1 | Sat 10 Aug 2019 | 0-1 v BrentfordMiddlesbrough 0-1 Brentford | Sky Bet Championship |
| 2 | Tue 13 Aug 2019 | 2-2 v Crewe AlexandraMiddlesbrough 2-2 Crewe Alexandra | Carabao Cup First Round |
| 3 | Tue 20 Aug 2019 | 1-0 v Wigan AthleticMiddlesbrough 1-0 Wigan Athletic | Sky Bet Championship |
| 4 | Sat 24 Aug 2019 | 1-1 v MillwallMiddlesbrough 1-1 Millwall | Sky Bet Championship |
| 5 | Sat 21 Sep 2019 | 0-1 v Cardiff CityCardiff City 1-0 Middlesbrough | Sky Bet Championship |
| 6 | Sat 28 Sep 2019 | 1-4 v Sheffield WednesdayMiddlesbrough 1-4 Sheffield Wednesday | Sky Bet Championship |
| 7 | Tue 1 Oct 2019 | 1-1 v Preston North EndMiddlesbrough 1-1 Preston North End | Sky Bet Championship |
| 8 | Fri 4 Oct 2019 | 1-2 v Birmingham CityBirmingham City 2-1 Middlesbrough | Sky Bet Championship |
| 9 | Sat 19 Oct 2019 | 0-1 v West Bromwich AlbionMiddlesbrough 0-1 West Bromwich Albion | Sky Bet Championship |
| 10 | Sat 26 Oct 2019 | 0-0 v FulhamMiddlesbrough 0-0 Fulham | Sky Bet Championship |
| 11 | Sat 2 Nov 2019 | 0-2 v Derby CountyDerby County 2-0 Middlesbrough | Sky Bet Championship |
| 12 | Sat 14 Dec 2019 | 1-3 v Swansea CitySwansea City 3-1 Middlesbrough | Sky Bet Championship |
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