| Middlesbrough FC v Reading FC 14/09/2019 | View match | |
| Cardiff City FC v Middlesbrough FC 21/09/2019 | £7.50 | |
| Middlesbrough FC v Sheffield Wednesday FC 28/09/2019 | View match | |
| Middlesbrough FC v Preston North End FC 01/10/2019 | View match | |
| Birmingham City FC v Middlesbrough FC 04/10/2019 | View match | |
| Middlesbrough FC v West Bromwich Albion FC 19/10/2019 | View match | |
| Huddersfield Town FC v Middlesbrough FC 23/10/2019 | £6.75 | |
| Middlesbrough FC v Fulham FC 26/10/2019 | View match | |
| Derby County FC v Middlesbrough FC 02/11/2019 | View match | |
| Queens Park Rangers FC v Middlesbrough FC 09/11/2019 | View match | |
| Middlesbrough FC v Hull City FC 24/11/2019 | View match | |
| Middlesbrough FC v Barnsley FC 27/11/2019 | View match |