| 1. Round | 08/08/2023 | Huddersfield Town | - | Middlesbrough FC | 2:3 | ||||
| Quarter-finals | 19/12/2023 | Port Vale FC | - | Middlesbrough FC | 0:3 |  |
|||
| Semi-finals | 09/01/2024 | Middlesbrough FC | - | Chelsea FC | 1:0 | ||||
| Semi-finals | 23/01/2024 | Chelsea FC | - | Middlesbrough FC | 6:1 |
| 1. Round | 08/08/2023 | Huddersfield Town | - | Middlesbrough FC | 2:3 | ||||
| Quarter-finals | 19/12/2023 | Port Vale FC | - | Middlesbrough FC | 0:3 | |
|||
| Semi-finals | 09/01/2024 | Middlesbrough FC | - | Chelsea FC | 1:0 | ||||
| Semi-finals | 23/01/2024 | Chelsea FC | - | Middlesbrough FC | 6:1 |
| Jonathan Mark Howson | |
| Born: | 21.05.1988 |
| Place of birth: |
Morley, 
England |
| Nationality: |
England
|
| Height: | 180 cm |
| Weight: | 77 kg |
| Position(s): | Central Midfielder Offensive Midfielder |
| Foot: | right |
