| 1 | Sat 14 Sep | 251-1 v Preston North EndMiddlesbrough 1-1 Preston North End | Sky Bet Championship |
| 2 | Sat 21 Sep | 250-1 v SunderlandSunderland 1-0 Middlesbrough | Sky Bet Championship |
| 3 | Sat 28 Sep | 25 2-0 v Stoke CityMiddlesbrough 2-0 Stoke City | Sky Bet Championship |
| 4 | Tue 1 Oct | 251-0 v West Bromwich AlbionWest Bromwich Albion 0-1 Middlesbrough | Sky Bet Championship |
| 5 | Sat 5 Oct | 251-2 v WatfordWatford 2-1 Middlesbrough | Sky Bet Championship |
| 6 | Sat 19 Oct | 250-2 v Bristol CityMiddlesbrough 0-2 Bristol City | Sky Bet Championship |
| 7 | Wed 23 Oct | 251-0 v Sheffield UnitedMiddlesbrough 1-0 Sheffield United | Sky Bet Championship |
| 8 | Sun 27 Oct | 25 3-3 v Norwich CityNorwich City 3-3 Middlesbrough | Sky Bet Championship |
| 9 | Sat 2 Nov | 25 0-3 v Coventry CityMiddlesbrough 0-3 Coventry City | Sky Bet Championship |
| 10 | Tue 5 Nov | 254-1 v Queens Park RangersQueens Park Rangers 1-4 Middlesbrough | Sky Bet Championship |
| 11 | Sat 9 Nov | 255-1 v Luton TownMiddlesbrough 5-1 Luton Town | Sky Bet Championship |
| 12 | Sat 23 Nov | 25 6-2 v Oxford UnitedOxford United 2-6 Middlesbrough | Sky Bet Championship |
| 13 | Wed 27 Nov | 250-1 v Blackburn RoversMiddlesbrough 0-1 Blackburn Rovers | Sky Bet Championship |
| 14 | Sat 30 Nov | 253-1 v Hull CityMiddlesbrough 3-1 Hull City | Sky Bet Championship |
| 15 | Fri 6 Dec | 251-1 v BurnleyBurnley 1-1 Middlesbrough | Sky Bet Championship |
| 16 | Tue 10 Dec | 25 1-3 v Leeds UnitedLeeds United 3-1 Middlesbrough | Sky Bet Championship |
| 17 | Sat 14 Dec | 251-0 v MillwallMiddlesbrough 1-0 Millwall | Sky Bet Championship |
| 18 | Sat 21 Dec | 25 3-3 v Plymouth ArgylePlymouth Argyle 3-3 Middlesbrough | Sky Bet Championship |
| 19 | Sun 29 Dec | 25 0-0 v BurnleyMiddlesbrough 0-0 Burnley | Sky Bet Championship |
| 20 | Sat 11 Jan | 250-1 v Blackburn RoversMiddlesbrough 0-1 Blackburn Rovers | Emirates FA Cup Third Round |
| 21 | Sat 18 Jan | 25 1-2 v PortsmouthPortsmouth 2-1 Middlesbrough | Sky Bet Championship |
| 22 | Mon 3 Feb | 252-3 v SunderlandMiddlesbrough 2-3 Sunderland | Sky Bet Championship |
| 23 | Wed 12 Feb | 25 1-3 v Sheffield UnitedSheffield United 3-1 Middlesbrough | Sky Bet Championship |
| 24 | Sat 15 Feb | 250-1 v WatfordMiddlesbrough 0-1 Watford | Sky Bet Championship |
| 25 | Tue 25 Feb | 253-1 v Stoke CityStoke City 1-3 Middlesbrough | Sky Bet Championship |
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