| 1 | Wed 14 Aug | 43-0 v Leeds UnitedLeeds United 0-3 Middlesbrough | Carabao Cup First Round |
| 2 | Sat 17 Aug | 40-1 v Derby CountyDerby County 1-0 Middlesbrough | Sky Bet Championship |
| 3 | Sat 24 Aug | 42-2 v PortsmouthMiddlesbrough 2-2 Portsmouth | Sky Bet Championship |
| 4 | Tue 27 Aug | 40-5 v Stoke CityMiddlesbrough 0-5 Stoke City | Carabao Cup Second Round |
| 5 | Sat 14 Sep | 41-1 v Preston North EndMiddlesbrough 1-1 Preston North End | Sky Bet Championship |
| 6 | Sat 28 Sep | 42-0 v Stoke CityMiddlesbrough 2-0 Stoke City | Sky Bet Championship |
| 7 | Sat 2 Nov | 40-3 v Coventry CityMiddlesbrough 0-3 Coventry City | Sky Bet Championship |
| 8 | Tue 5 Nov | 44-1 v Queens Park RangersQueens Park Rangers 1-4 Middlesbrough | Sky Bet Championship |
| 9 | Sat 9 Nov | 45-1 v Luton TownMiddlesbrough 5-1 Luton Town | Sky Bet Championship |
| 10 | Sat 23 Nov | 46-2 v Oxford UnitedOxford United 2-6 Middlesbrough | Sky Bet Championship |
| 11 | Wed 27 Nov | 40-1 v Blackburn RoversMiddlesbrough 0-1 Blackburn Rovers | Sky Bet Championship |
| 12 | Sat 30 Nov | 43-1 v Hull CityMiddlesbrough 3-1 Hull City | Sky Bet Championship |
| 13 | Fri 6 Dec | 41-1 v BurnleyBurnley 1-1 Middlesbrough | Sky Bet Championship |
| 14 | Tue 10 Dec | 41-3 v Leeds UnitedLeeds United 3-1 Middlesbrough | Sky Bet Championship |
| 15 | Sat 21 Dec | 43-3 v Plymouth ArgylePlymouth Argyle 3-3 Middlesbrough | Sky Bet Championship |
| 16 | Thu 26 Dec | 43-3 v Sheffield WednesdayMiddlesbrough 3-3 Sheffield Wednesday | Sky Bet Championship |
| 17 | Sun 29 Dec | 40-0 v BurnleyMiddlesbrough 0-0 Burnley | Sky Bet Championship |
| 18 | Wed 1 Jan | 4 1-0 v Hull CityHull City 0-1 Middlesbrough | Sky Bet Championship |
| 19 | Sat 4 Jan | 4 1-1 v Cardiff CityMiddlesbrough 1-1 Cardiff City | Sky Bet Championship |
| 20 | Sat 11 Jan | 40-1 v Blackburn RoversMiddlesbrough 0-1 Blackburn Rovers | Emirates FA Cup Third Round |
| 21 | Sat 18 Jan | 41-2 v PortsmouthPortsmouth 2-1 Middlesbrough | Sky Bet Championship |
| 22 | Tue 21 Jan | 42-0 v West Bromwich AlbionMiddlesbrough 2-0 West Bromwich Albion | Sky Bet Championship |
| 23 | Wed 12 Feb | 41-3 v Sheffield UnitedSheffield United 3-1 Middlesbrough | Sky Bet Championship |
| 24 | Sat 15 Feb | 40-1 v WatfordMiddlesbrough 0-1 Watford | Sky Bet Championship |
| 25 | Tue 11 Mar | 42-1 v Queens Park RangersMiddlesbrough 2-1 Queens Park Rangers | Sky Bet Championship |
| 26 | Fri 4 Apr | 42-0 v Blackburn RoversBlackburn Rovers 0-2 Middlesbrough | Sky Bet Championship |
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