| 1. Round | 10/08/2018 | Southampton FC U23 | - | Middlesbrough FC U23 | 2:0 | ||||
| 2. Round | 17/08/2018 | Middlesbrough FC U23 | - | Fulham FC U23 | 4:3 | ||||
| 4. Round | 02/09/2018 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:2 |  |
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| 5. Round | 17/09/2018 | West Bromwich Albion U23 | - | Middlesbrough FC U23 | 2:3 | ||||
| 6. Round | 23/09/2018 | Middlesbrough FC U23 | - | Manchester United U23 | 0:2 | ||||
| 7. Round | 28/09/2018 | Wolverhampton Wanderers U23 | - | Middlesbrough FC U23 | 2:0 | ||||
| 8. Round | 19/10/2018 | Middlesbrough FC U23 | - | Reading FC U23 | 2:3 | ||||
| 9. Round | 26/10/2018 | Newcastle United U23 | - | Middlesbrough FC U23 | 1:3 | ||||
| 10. Round | 04/11/2018 | Middlesbrough FC U23 | - | Norwich City U23 | 2:1 | ||||
| 11. Round | 26/11/2018 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 1:3 | |
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| 12. Round | 07/12/2018 | Manchester United U23 | - | Middlesbrough FC U23 | 2:0 | ||||
| 13. Round | 14/12/2018 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 2:2 | |
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| 15. Round | 13/01/2019 | Middlesbrough FC U23 | - | Southampton FC U23 | 1:2 |
England