| 1 | Sat 11 Jan 2020 | 2-2 v Derby CountyMiddlesbrough 2-2 Derby County | Sky Bet Championship |
| 2 | Tue 14 Jan 2020 | 1-2 v Tottenham HotspurTottenham Hotspur 2-1 Middlesbrough | Emirates FA Cup Third Round Replay |
| 3 | Fri 17 Jan 2020 | 0-1 v FulhamFulham 1-0 Middlesbrough | Sky Bet Championship |
| 4 | Tue 21 Jan 2020 | 1-1 v Birmingham CityMiddlesbrough 1-1 Birmingham City | Sky Bet Championship |
| 5 | Sat 1 Feb 2020 | 1-1 v Blackburn RoversMiddlesbrough 1-1 Blackburn Rovers | Sky Bet Championship |
| 6 | Sat 8 Feb 2020 | 2-3 v BrentfordBrentford 3-2 Middlesbrough | Sky Bet Championship |
| 7 | Tue 11 Feb 2020 | 2-2 v Wigan AthleticWigan Athletic 2-2 Middlesbrough | Sky Bet Championship |
| 8 | Sat 15 Feb 2020 | 0-1 v Luton TownMiddlesbrough 0-1 Luton Town | Sky Bet Championship |
| 9 | Wed 26 Feb 2020 | 0-1 v Leeds UnitedMiddlesbrough 0-1 Leeds United | Sky Bet Championship |
| 10 | Sat 20 Jun 2020 | 20 0-3 v Swansea CityMiddlesbrough 0-3 Swansea City | Sky Bet Championship |
| 11 | Sun 5 Jul 2020 | 200-1 v Queens Park RangersMiddlesbrough 0-1 Queens Park Rangers | Sky Bet Championship |
| 12 | Sat 18 Jul 2020 | 201-3 v Cardiff CityMiddlesbrough 1-3 Cardiff City | Sky Bet Championship |
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