| 1 | Tue 14 Aug 2018 | 43-3 v Notts CountyMiddlesbrough 3-3 Notts County | Carabao Cup First Round |
| 2 | Fri 24 Aug 2018 | 4 1-0 v West Bromwich AlbionMiddlesbrough 1-0 West Bromwich Albion | Sky Bet Championship |
| 3 | Tue 28 Aug 2018 | 42-1 v RochdaleMiddlesbrough 2-1 Rochdale | Carabao Cup Second Round |
| 4 | Fri 31 Aug 2018 | 4 0-0 v Leeds UnitedLeeds United 0-0 Middlesbrough | Sky Bet Championship |
| 5 | Sat 15 Sep 2018 | 40-1 v Norwich CityNorwich City 1-0 Middlesbrough | Sky Bet Championship |
| 6 | Wed 19 Sep 2018 | 42-0 v Bolton WanderersMiddlesbrough 2-0 Bolton Wanderers | Sky Bet Championship |
| 7 | Sat 22 Sep 2018 | 40-0 v Swansea CityMiddlesbrough 0-0 Swansea City | Sky Bet Championship |
| 8 | Sat 29 Sep 2018 | 41-1 v Hull CityHull City 1-1 Middlesbrough | Sky Bet Championship |
| 9 | Tue 2 Oct 2018 | 42-0 v Ipswich TownIpswich Town 0-2 Middlesbrough | Sky Bet Championship |
| 10 | Sat 6 Oct 2018 | 4 0-2 v Nottingham ForestMiddlesbrough 0-2 Nottingham Forest | Sky Bet Championship |
| 11 | Fri 19 Oct 2018 | 4 2-1 v Sheffield WednesdaySheffield Wednesday 1-2 Middlesbrough | Sky Bet Championship |
| 12 | Tue 23 Oct 2018 | 40-0 v Rotherham UnitedMiddlesbrough 0-0 Rotherham United | Sky Bet Championship |
| 13 | Sat 27 Oct 2018 | 4 1-1 v Derby CountyMiddlesbrough 1-1 Derby County | Sky Bet Championship |
| 14 | Wed 31 Oct 2018 | 41-0 v Crystal PalaceMiddlesbrough 1-0 Crystal Palace | Carabao Cup Fourth Round |
| 15 | Sat 24 Nov 2018 | 42-1 v BrentfordBrentford 1-2 Middlesbrough | Sky Bet Championship |
| 16 | Tue 27 Nov 2018 | 41-1 v Preston North EndPreston North End 1-1 Middlesbrough | Sky Bet Championship |
| 17 | Sat 8 Dec 2018 | 41-1 v Blackburn RoversMiddlesbrough 1-1 Blackburn Rovers | Sky Bet Championship |
| 18 | Sat 15 Dec 2018 | 41-2 v Queens Park RangersQueens Park Rangers 2-1 Middlesbrough | Sky Bet Championship |
| 19 | Sat 22 Dec 2018 | 41-0 v ReadingReading 0-1 Middlesbrough | Sky Bet Championship |
| 20 | Wed 26 Dec 2018 | 4 0-1 v Sheffield WednesdayMiddlesbrough 0-1 Sheffield Wednesday | Sky Bet Championship |
| 21 | Sat 29 Dec 2018 | 42-0 v Ipswich TownMiddlesbrough 2-0 Ipswich Town | Sky Bet Championship |
| 22 | Tue 1 Jan 2019 | 41-1 v Derby CountyDerby County 1-1 Middlesbrough | Sky Bet Championship |
| 23 | Sat 5 Jan 2019 | 45-0 v Peterborough UnitedMiddlesbrough 5-0 Peterborough United | Emirates FA Cup Third Round |
| 24 | Sat 12 Jan 2019 | 42-1 v Birmingham CityBirmingham City 1-2 Middlesbrough | Sky Bet Championship |
| 25 | Sat 19 Jan 2019 | 4 1-1 v MillwallMiddlesbrough 1-1 Millwall | Sky Bet Championship |
| 26 | Sat 26 Jan 2019 | 41-1 v Newport CountyMiddlesbrough 1-1 Newport County | Emirates FA Cup Fourth Round |
| 27 | Sat 2 Feb 2019 | 43-2 v West Bromwich AlbionWest Bromwich Albion 2-3 Middlesbrough | Sky Bet Championship |
| 28 | Tue 5 Feb 2019 | 40-2 v Newport CountyNewport County 2-0 Middlesbrough | Emirates FA Cup Fourth Round |
| 29 | Sat 9 Feb 2019 | 41-1 v Leeds UnitedMiddlesbrough 1-1 Leeds United | Sky Bet Championship |
| 30 | Wed 13 Feb 2019 | 4 0-1 v Sheffield UnitedSheffield United 1-0 Middlesbrough | Sky Bet Championship |
| 31 | Sat 23 Feb 2019 | 42-0 v Queens Park RangersMiddlesbrough 2-0 Queens Park Rangers | Sky Bet Championship |
| 32 | Sat 2 Mar 2019 | 4 0-0 v Wigan AthleticWigan Athletic 0-0 Middlesbrough | Sky Bet Championship |
| 33 | Sat 9 Mar 2019 | 4 1-2 v BrentfordMiddlesbrough 1-2 Brentford | Sky Bet Championship |
| 34 | Wed 13 Mar 2019 | 4 1-2 v Preston North EndMiddlesbrough 1-2 Preston North End | Sky Bet Championship |
| 35 | Sat 16 Mar 2019 | 40-3 v Aston VillaAston Villa 3-0 Middlesbrough | Sky Bet Championship |
| 36 | Sat 30 Mar 2019 | 4 0-1 v Norwich CityMiddlesbrough 0-1 Norwich City | Sky Bet Championship |
| 37 | Sat 6 Apr 2019 | 41-3 v Swansea CitySwansea City 3-1 Middlesbrough | Sky Bet Championship |
| 38 | Tue 9 Apr 2019 | 42-0 v Bolton WanderersBolton Wanderers 0-2 Middlesbrough | Sky Bet Championship |
| 39 | Sat 13 Apr 2019 | 41-0 v Hull CityMiddlesbrough 1-0 Hull City | Sky Bet Championship |
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