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| Blackpool FC v Middlesbrough FC 11/08/2021 | £7.50 | |
| Middlesbrough FC v Bristol City FC 14/08/2021 | View match | |
| Middlesbrough FC v Queens Park Rangers FC 18/08/2021 | View match | |
| Derby County FC v Middlesbrough FC 21/08/2021 | View match | |
| Middlesbrough FC v Blackburn Rovers FC 28/08/2021 | £7.50 | |
| Coventry City FC v Middlesbrough FC 11/09/2021 | View match | |
| Nottingham Forest FC v Middlesbrough FC 15/09/2021 | View match | |
| 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 |