| 1 | Fri 5 Dec | 144-1 v Hull CityHull City 1-4 Middlesbrough | Sky Bet Championship |
| 2 | Tue 9 Dec | 142-1 v Charlton AthleticCharlton Athletic 1-2 Middlesbrough | Sky Bet Championship |
| 3 | Sat 13 Dec | 143-1 v Queens Park RangersMiddlesbrough 3-1 Queens Park Rangers | Sky Bet Championship |
| 4 | Sat 20 Dec | 140-2 v Bristol CityBristol City 2-0 Middlesbrough | Sky Bet Championship |
| 5 | Fri 26 Dec | 14 0-0 v Blackburn RoversMiddlesbrough 0-0 Blackburn Rovers | Sky Bet Championship |
| 6 | Mon 29 Dec | 140-1 v Hull CityMiddlesbrough 0-1 Hull City | Sky Bet Championship |
| 7 | Thu 1 Jan | 14 0-1 v Derby CountyDerby County 1-0 Middlesbrough | Sky Bet Championship |
| 8 | Sun 4 Jan | 144-0 v SouthamptonMiddlesbrough 4-0 Southampton | Sky Bet Championship |
| 9 | Sat 10 Jan | 14 1-3 v FulhamFulham 3-1 Middlesbrough | Emirates FA Cup Third Round |
| 10 | Fri 16 Jan | 143-2 v West Bromwich AlbionWest Bromwich Albion 2-3 Middlesbrough | Sky Bet Championship |
| 11 | Wed 21 Jan | 142-1 v Stoke CityStoke City 1-2 Middlesbrough | Sky Bet Championship |
| 12 | Sat 24 Jan | 144-0 v Preston North EndMiddlesbrough 4-0 Preston North End | Sky Bet Championship |
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