| 1e Ronde | 08.08.2023 | Huddersfield Town | - | Middlesbrough FC | 2:3 |  |
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| 2e Ronde | 29.08.2023 | Bolton Wanderers | - | Middlesbrough FC | 1:3 | ||||
| 3e Ronde | 26.09.2023 | Bradford City | - | Middlesbrough FC | 0:2 | ||||
| Achtste finale | 31.10.2023 | Exeter City | - | Middlesbrough FC | 2:3 | |
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| Kwartfinale | 19.12.2023 | Port Vale FC | - | Middlesbrough FC | 0:3 |
Engeland