| Middlesbrough FC v Blackpool FC 18/09/2021 | View match | |
| Reading FC v Middlesbrough FC 25/09/2021 | View match | |
| Middlesbrough FC v Sheffield United FC 28/09/2021 | View match | |
| Hull City FC v Middlesbrough FC 02/10/2021 | View match | |
| Middlesbrough FC v Peterborough United FC 16/10/2021 | View match | |
| Middlesbrough FC v Barnsley FC 20/10/2021 | View match | |
| Cardiff City FC v Middlesbrough FC 23/10/2021 | £8.00 | |
| Middlesbrough FC v Birmingham City FC 30/10/2021 | View match | |
| Luton Town FC v Middlesbrough FC 02/11/2021 | £7.50 | |
| West Bromwich Albion FC v Middlesbrough FC 06/11/2021 | View match | |
| Middlesbrough FC v Millwall FC 20/11/2021 | View match | |
| Middlesbrough FC v Preston North End FC 23/11/2021 | View match |