| 1 | Sat 15 Aug | 142-1 v Lincoln CityMiddlesbrough 2-1 Lincoln City | Sky Bet Championship |
| 2 | Sat 22 Aug | 141-2 v Blackburn RoversBlackburn Rovers 2-1 Middlesbrough | Sky Bet Championship |
| 3 | Tue 25 Aug | 14 3-1 v Doncaster RoversDoncaster Rovers 1-3 Middlesbrough | Carabao Cup Second Round |
| 4 | Sat 29 Aug | 143-1 v West Bromwich AlbionMiddlesbrough 3-1 West Bromwich Albion | Sky Bet Championship |
| 5 | Sat 5 Sep | 141-0 v Queens Park RangersQueens Park Rangers 0-1 Middlesbrough | Sky Bet Championship |
| 6 | Tue 8 Sep | 14 0-3 v Crystal PalaceCrystal Palace 3-0 Middlesbrough | Carabao Cup Third Round |
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