| Luton Town FC v Middlesbrough FC 24/04/2023 | £8.00 | |
| Rotherham United FC v Middlesbrough FC 01/05/2023 | View match | |
| Middlesbrough FC v Coventry City FC 08/05/2023 | View match | |
| Coventry City FC v Middlesbrough FC 14/05/2023 | View match | |
| Middlesbrough FC v Coventry City FC 17/05/2023 | £0.00 | |
| Middlesbrough FC v Millwall FC 05/08/2023 | View match | |
| Huddersfield Town FC v Middlesbrough FC 08/08/2023 | £9.50 | |
| Coventry City FC v Middlesbrough FC 12/08/2023 | View match | |
| Middlesbrough FC v Huddersfield Town FC 19/08/2023 | View match | |
| West Bromwich Albion FC v Middlesbrough FC 26/08/2023 | View match | |
| Bolton Wanderers FC v Middlesbrough FC 29/08/2023 | View match | |
| Middlesbrough FC v Queens Park Rangers FC 02/09/2023 | View match |