| 1 | Sat 10 Aug | 51-0 v Swansea CityMiddlesbrough 1-0 Swansea City | Sky Bet Championship |
| 2 | Wed 14 Aug | 53-0 v Leeds UnitedLeeds United 0-3 Middlesbrough | Carabao Cup First Round |
| 3 | Sat 17 Aug | 50-1 v Derby CountyDerby County 1-0 Middlesbrough | Sky Bet Championship |
| 4 | Sat 24 Aug | 52-2 v PortsmouthMiddlesbrough 2-2 Portsmouth | Sky Bet Championship |
| 5 | Tue 27 Aug | 50-5 v Stoke CityMiddlesbrough 0-5 Stoke City | Carabao Cup Second Round |
| 6 | Sat 31 Aug | 52-0 v Cardiff CityCardiff City 0-2 Middlesbrough | Sky Bet Championship |
| 7 | Sat 14 Sep | 51-1 v Preston North EndMiddlesbrough 1-1 Preston North End | Sky Bet Championship |
| 8 | Sat 21 Sep | 50-1 v SunderlandSunderland 1-0 Middlesbrough | Sky Bet Championship |
| 9 | Wed 23 Oct | 51-0 v Sheffield UnitedMiddlesbrough 1-0 Sheffield United | Sky Bet Championship |
| 10 | Sat 2 Nov | 50-3 v Coventry CityMiddlesbrough 0-3 Coventry City | Sky Bet Championship |
| 11 | Tue 5 Nov | 54-1 v Queens Park RangersQueens Park Rangers 1-4 Middlesbrough | Sky Bet Championship |
| 12 | Sat 9 Nov | 55-1 v Luton TownMiddlesbrough 5-1 Luton Town | Sky Bet Championship |
| 13 | Sat 23 Nov | 56-2 v Oxford UnitedOxford United 2-6 Middlesbrough | Sky Bet Championship |
| 14 | Wed 27 Nov | 50-1 v Blackburn RoversMiddlesbrough 0-1 Blackburn Rovers | Sky Bet Championship |
| 15 | Tue 10 Dec | 51-3 v Leeds UnitedLeeds United 3-1 Middlesbrough | Sky Bet Championship |
| 16 | Thu 26 Dec | 53-3 v Sheffield WednesdayMiddlesbrough 3-3 Sheffield Wednesday | Sky Bet Championship |
| 17 | Sat 11 Jan | 50-1 v Blackburn RoversMiddlesbrough 0-1 Blackburn Rovers | Emirates FA Cup Third Round |
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