| Middlesbrough FC v Birmingham City FC 21/10/2023 | View match | |
| Norwich City FC v Middlesbrough FC 24/10/2023 | View match | |
| Middlesbrough FC v Stoke City FC 28/10/2023 | View match | |
| Exeter City FC v Middlesbrough FC 30/10/2023 | View match | |
| Plymouth Argyle FC v Middlesbrough FC 04/11/2023 | View match | |
| Middlesbrough FC v Leicester City FC 11/11/2023 | View match | |
| Bristol City FC v Middlesbrough FC 25/11/2023 | £8.50 | |
| Middlesbrough FC v Preston North End FC 28/11/2023 | View match | |
| Leeds United FC v Middlesbrough FC 02/12/2023 | View match | |
| Middlesbrough FC v Ipswich Town FC 09/12/2023 | £9.50 | |
| Middlesbrough FC v Hull City FC 13/12/2023 | View match | |
| Swansea City FC v Middlesbrough FC 16/12/2023 | View match |