| Derby County FC v Middlesbrough FC 01/01/2019 | View match | |
| Middlesbrough FC v Peterborough United FC 05/01/2019 | £6.50 | |
| Birmingham City FC v Middlesbrough FC 12/01/2019 | View match | |
| Middlesbrough FC v Millwall FC 19/01/2019 | £6.50 | |
| Middlesbrough FC v Newport County AFC 26/01/2019 | View match | |
| West Bromwich Albion FC v Middlesbrough FC 02/02/2019 | View match | |
| Newport County AFC v Middlesbrough FC 05/02/2019 | £6.50 | |
| Middlesbrough FC v Leeds United FC 09/02/2019 | View match | |
| Sheffield United FC v Middlesbrough FC 13/02/2019 | View match | |
| Blackburn Rovers FC v Middlesbrough FC 17/02/2019 | View match | |
| Middlesbrough FC v Queens Park Rangers FC 23/02/2019 | View match | |
| Wigan Athletic FC v Middlesbrough FC 02/03/2019 | View match |