| Middlesbrough FC v Blackburn Rovers FC 24/01/2021 | View match | |
| Middlesbrough FC v Rotherham United FC 27/01/2021 | View match | |
| Norwich City FC v Middlesbrough FC 30/01/2021 | View match | |
| Middlesbrough FC v Brentford FC 06/02/2021 | £7.50 | |
| Derby County FC v Middlesbrough FC 13/02/2021 | View match | |
| Middlesbrough FC v Huddersfield Town FC 16/02/2021 | View match | |
| Reading FC v Middlesbrough FC 20/02/2021 | View match | |
| Middlesbrough FC v Bristol City FC 23/02/2021 | View match | |
| Middlesbrough FC v Cardiff City FC 27/02/2021 | View match | |
| Coventry City FC v Middlesbrough FC 02/03/2021 | View match | |
| Swansea City FC v Middlesbrough FC 06/03/2021 | £7.50 | |
| Middlesbrough FC v Stoke City FC 13/03/2021 | View match |