| 1 | Tue 24 Jul 2018 | 2-3 v RochdaleRochdale 3-2 Middlesbrough | Friendly |
| 2 | Sat 4 Aug 2018 | 262-2 v MillwallMillwall 2-2 Middlesbrough | Sky Bet Championship |
| 3 | Tue 7 Aug 2018 | 263-0 v Sheffield UnitedMiddlesbrough 3-0 Sheffield United | Sky Bet Championship |
| 4 | Sat 11 Aug 2018 | 261-0 v Birmingham CityMiddlesbrough 1-0 Birmingham City | Sky Bet Championship |
| 5 | Sat 18 Aug 2018 | 262-0 v Bristol CityBristol City 0-2 Middlesbrough | Sky Bet Championship |
| 6 | Tue 25 Sep 2018 | 262-2 v Preston North EndPreston North End 2-2 Middlesbrough | Carabao Cup Third Round |
| 7 | Wed 31 Oct 2018 | 261-0 v Crystal PalaceMiddlesbrough 1-0 Crystal Palace | Carabao Cup Fourth Round |
| 8 | Sat 3 Nov 2018 | 260-0 v Stoke CityStoke City 0-0 Middlesbrough | Sky Bet Championship |
| 9 | Sat 10 Nov 2018 | 262-0 v Wigan AthleticMiddlesbrough 2-0 Wigan Athletic | Sky Bet Championship |
| 10 | Sat 24 Nov 2018 | 262-1 v BrentfordBrentford 1-2 Middlesbrough | Sky Bet Championship |
| 11 | Tue 27 Nov 2018 | 261-1 v Preston North EndPreston North End 1-1 Middlesbrough | Sky Bet Championship |
| 12 | Sat 8 Dec 2018 | 261-1 v Blackburn RoversMiddlesbrough 1-1 Blackburn Rovers | Sky Bet Championship |
| 13 | Sat 15 Dec 2018 | 261-2 v Queens Park RangersQueens Park Rangers 2-1 Middlesbrough | Sky Bet Championship |
| 14 | Tue 18 Dec 2018 | 260-1 v Burton AlbionMiddlesbrough 0-1 Burton Albion | Carabao Cup Quarter Final |
| 15 | Sat 22 Dec 2018 | 261-0 v ReadingReading 0-1 Middlesbrough | Sky Bet Championship |
| 16 | Wed 26 Dec 2018 | 260-1 v Sheffield WednesdayMiddlesbrough 0-1 Sheffield Wednesday | Sky Bet Championship |
| 17 | Sat 29 Dec 2018 | 262-0 v Ipswich TownMiddlesbrough 2-0 Ipswich Town | Sky Bet Championship |
| 18 | Tue 1 Jan 2019 | 261-1 v Derby CountyDerby County 1-1 Middlesbrough | Sky Bet Championship |
| 19 | Sat 12 Jan 2019 | 26 2-1 v Birmingham CityBirmingham City 1-2 Middlesbrough | Sky Bet Championship |
| 20 | Sat 19 Jan 2019 | 261-1 v MillwallMiddlesbrough 1-1 Millwall | Sky Bet Championship |
| 21 | Sat 26 Jan 2019 | 261-1 v Newport CountyMiddlesbrough 1-1 Newport County | Emirates FA Cup Fourth Round |
| 22 | Sat 2 Feb 2019 | 26 3-2 v West Bromwich AlbionWest Bromwich Albion 2-3 Middlesbrough | Sky Bet Championship |
| 23 | Tue 5 Feb 2019 | 260-2 v Newport CountyNewport County 2-0 Middlesbrough | Emirates FA Cup Fourth Round |
| 24 | Sat 9 Feb 2019 | 261-1 v Leeds UnitedMiddlesbrough 1-1 Leeds United | Sky Bet Championship |
| 25 | Wed 13 Feb 2019 | 260-1 v Sheffield UnitedSheffield United 1-0 Middlesbrough | Sky Bet Championship |
| 26 | Sun 17 Feb 2019 | 261-0 v Blackburn RoversBlackburn Rovers 0-1 Middlesbrough | Sky Bet Championship |
| 27 | Sat 23 Feb 2019 | 262-0 v Queens Park RangersMiddlesbrough 2-0 Queens Park Rangers | Sky Bet Championship |
| 28 | Sat 2 Mar 2019 | 260-0 v Wigan AthleticWigan Athletic 0-0 Middlesbrough | Sky Bet Championship |
| 29 | Sat 9 Mar 2019 | 261-2 v BrentfordMiddlesbrough 1-2 Brentford | Sky Bet Championship |
| 30 | Wed 13 Mar 2019 | 261-2 v Preston North EndMiddlesbrough 1-2 Preston North End | Sky Bet Championship |
| 31 | Sat 16 Mar 2019 | 260-3 v Aston VillaAston Villa 3-0 Middlesbrough | Sky Bet Championship |
| 32 | Tue 2 Apr 2019 | 260-1 v Bristol CityMiddlesbrough 0-1 Bristol City | Sky Bet Championship |
| 33 | Sat 27 Apr 2019 | 262-1 v ReadingMiddlesbrough 2-1 Reading | Sky Bet Championship |
| 34 | Sun 5 May 2019 | 262-1 v Rotherham UnitedRotherham United 1-2 Middlesbrough | Sky Bet Championship |
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