| 1. Runde | 08.08.2023 | Huddersfield Town | - | Middlesbrough FC | 2:3 | ||||
| 2. Runde | 29.08.2023 | Bolton Wanderers | - | Middlesbrough FC | 1:3 | ||||
| 3. Runde | 26.09.2023 | Bradford City | - | Middlesbrough FC | 0:2 | ||||
| Achtelfinale | 31.10.2023 | Exeter City | - | Middlesbrough FC | 2:3 | ||||
| Halbfinale | 09.01.2024 | Middlesbrough FC | - | Chelsea FC | 1:0 |  |
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| Halbfinale | 23.01.2024 | Chelsea FC | - | Middlesbrough FC | 6:1 |
England