1. Round | 08/08/2023 | Huddersfield Town | - | Middlesbrough FC | 2:3 | ![]() |
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2. Round | 29/08/2023 | Bolton Wanderers | - | Middlesbrough FC | 1:3 | ![]() |
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Round of 16 | 31/10/2023 | Exeter City | - | Middlesbrough FC | 2:3 | ||||
Quarter-finals | 19/12/2023 | Port Vale FC | - | Middlesbrough FC | 0:3 | ![]() |
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Semi-finals | 09/01/2024 | Middlesbrough FC | - | Chelsea FC | 1:0 | ||||
Semi-finals | 23/01/2024 | Chelsea FC | - | Middlesbrough FC | 6:1 | ![]() |