| 1 | Sat 26 Jan 2019 | 1-1 v Newport CountyMiddlesbrough 1-1 Newport County | Emirates FA Cup Fourth Round |
| 2 | Sat 2 Feb 2019 | 3-2 v West Bromwich AlbionWest Bromwich Albion 2-3 Middlesbrough | Sky Bet Championship |
| 3 | Sat 9 Feb 2019 | 1-1 v Leeds UnitedMiddlesbrough 1-1 Leeds United | Sky Bet Championship |
| 4 | Wed 13 Feb 2019 | 0-1 v Sheffield UnitedSheffield United 1-0 Middlesbrough | Sky Bet Championship |
| 5 | Sun 17 Feb 2019 | 1-0 v Blackburn RoversBlackburn Rovers 0-1 Middlesbrough | Sky Bet Championship |
| 6 | Sat 23 Feb 2019 | 2-0 v Queens Park RangersMiddlesbrough 2-0 Queens Park Rangers | Sky Bet Championship |
| 7 | Sat 2 Mar 2019 | 0-0 v Wigan AthleticWigan Athletic 0-0 Middlesbrough | Sky Bet Championship |
| 8 | Sat 9 Mar 2019 | 12 1-2 v BrentfordMiddlesbrough 1-2 Brentford | Sky Bet Championship |
| 9 | Wed 13 Mar 2019 | 121-2 v Preston North EndMiddlesbrough 1-2 Preston North End | Sky Bet Championship |
| 10 | Sat 16 Mar 2019 | 12 0-3 v Aston VillaAston Villa 3-0 Middlesbrough | Sky Bet Championship |
| 11 | Sat 30 Mar 2019 | 12 0-1 v Norwich CityMiddlesbrough 0-1 Norwich City | Sky Bet Championship |
| 12 | Tue 2 Apr 2019 | 120-1 v Bristol CityMiddlesbrough 0-1 Bristol City | Sky Bet Championship |
| 13 | Sat 6 Apr 2019 | 121-3 v Swansea CitySwansea City 3-1 Middlesbrough | Sky Bet Championship |
| 14 | Tue 9 Apr 2019 | 122-0 v Bolton WanderersBolton Wanderers 0-2 Middlesbrough | Sky Bet Championship |
| 15 | Sat 13 Apr 2019 | 121-0 v Hull CityMiddlesbrough 1-0 Hull City | Sky Bet Championship |
| 16 | Fri 19 Apr 2019 | 121-0 v Stoke CityMiddlesbrough 1-0 Stoke City | Sky Bet Championship |
| 17 | Mon 22 Apr 2019 | 120-3 v Nottingham ForestNottingham Forest 3-0 Middlesbrough | Sky Bet Championship |
| 18 | Sat 27 Apr 2019 | 122-1 v ReadingMiddlesbrough 2-1 Reading | Sky Bet Championship |
| 19 | Sun 5 May 2019 | 12 2-1 v Rotherham UnitedRotherham United 1-2 Middlesbrough | Sky Bet Championship |
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