| 3. Round | 24/08/2015 | Southampton FC U21 | - | Middlesbrough FC U21 | 1:1 |  |
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| 7. Round | 08/11/2015 | Middlesbrough FC U21 | - | Everton FC U21 | 1:0 | ||||
| 9. Round | 17/11/2015 | Norwich City U21 | - | Middlesbrough FC U21 | 0:5 | ||||
| 11. Round | 30/11/2015 | Middlesbrough FC U21 | - | Tottenham Hotspur U21 | 1:2 | ||||
| 5. Round | 21/12/2015 | Chelsea FC U21 | - | Middlesbrough FC U21 | 1:0 |  |
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| 14. Round | 08/01/2016 | Middlesbrough FC U21 | - | Norwich City U21 | 1:1 | ||||
| 2. Round | 11/04/2016 | Manchester United U21 | - | Middlesbrough FC U21 | 1:0 |
England