1. Round | 08/08/2023 | Huddersfield Town | - | Middlesbrough FC | 2:3 | ||||
2. Round | 29/08/2023 | Bolton Wanderers | - | Middlesbrough FC | 1:3 | ||||
3. Round | 26/09/2023 | Bradford City | - | Middlesbrough FC | 0:2 | ||||
Round of 16 | 31/10/2023 | Exeter City | - | Middlesbrough FC | 2:3 |