| 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 |  |
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| Achtste finale | 31.10.2023 | Exeter City | - | Middlesbrough FC | 2:3 | ||||
| Kwartfinale | 19.12.2023 | Port Vale FC | - | Middlesbrough FC | 0:3 | |
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| Halve Finale | 09.01.2024 | Middlesbrough FC | - | Chelsea FC | 1:0 | ||||
| Halve Finale | 23.01.2024 | Chelsea FC | - | Middlesbrough FC | 6:1 | |
Engeland