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| Date | Matchup | Venue |
|---|---|---|
| vs Lincoln City | Riverside Stadium, Middlesbrough | |
| @ Blackburn Rovers | Ewood Park, Blackburn | |
| vs West Bromwich Albion | Riverside Stadium, Middlesbrough | |
| @ Burnley | Turf Moor, Burnley | |
| @ Queens Park Rangers | MATRADE Loftus Road, London | |
| vs Millwall | Riverside Stadium, Middlesbrough | |
| vs Norwich City | Riverside Stadium, Middlesbrough | |
| @ Birmingham City | St. Andrew's Stadium, Birmingham | |
| vs Wolverhampton Wanderers | Riverside Stadium, Middlesbrough | |
| @ Stoke City | bet365 Stadium, Stoke-on-Trent | |
| vs Cardiff City | Riverside Stadium, Middlesbrough | |
| @ Bolton Wanderers | Toughsheet Community Stadium, Manchester | |
| vs Charlton Athletic | Riverside Stadium, Middlesbrough | |
| @ Wrexham | STōK Cae Ras, Wrexham | |
| @ Watford | Vicarage Road, Watford | |
| vs Bristol City | Riverside Stadium, Middlesbrough | |
| vs Swansea City | Riverside Stadium, Middlesbrough | |
| @ Southampton | St. Mary's Stadium, Southampton | |
| vs Derby County | Riverside Stadium, Middlesbrough | |
| @ West Ham United | London Stadium, London | |
| @ Preston North End | Deepdale, Preston | |
| vs Portsmouth | Riverside Stadium, Middlesbrough | |
| @ Sheffield United | Bramall Lane, Sheffield | |
| vs Bolton Wanderers | Riverside Stadium, Middlesbrough | |
| vs Preston North End | Riverside Stadium, Middlesbrough | |
| @ Cardiff City | Cardiff City Stadium, Cardiff | |
| @ Charlton Athletic | The Valley, London | |
| vs Wrexham | Riverside Stadium, Middlesbrough | |
| vs Watford | Riverside Stadium, Middlesbrough | |
| @ Bristol City | Ashton Gate, Bristol | |
| @ Norwich City | Carrow Road, Norwich | |
| vs Stoke City | Riverside Stadium, Middlesbrough | |
| vs Birmingham City | Riverside Stadium, Middlesbrough | |
| @ Wolverhampton Wanderers | Molineux Stadium, Wolverhampton | |
| vs Blackburn Rovers | Riverside Stadium, Middlesbrough | |
| @ Lincoln City | LNER Stadium, Lincoln | |
| vs Southampton | Riverside Stadium, Middlesbrough | |
| @ Derby County | Pride Park, Derby | |
| vs Sheffield United | Riverside Stadium, Middlesbrough | |
| @ Portsmouth | Fratton Park, Portsmouth | |
| @ Millwall | The Den, London | |
| vs Queens Park Rangers | Riverside Stadium, Middlesbrough | |
| @ West Bromwich Albion | The Hawthorns, West Bromwich | |
| vs Burnley | Riverside Stadium, Middlesbrough | |
| vs West Ham United | Riverside Stadium, Middlesbrough | |
| @ Swansea City | Swansea.com Stadium, Swansea |