| FA Cup | 24/01/09 | Wolverhampton Wanderers | - | Middlesbrough FC | 1:2 | ||||
| Championship | 21/10/14 | Wolverhampton Wanderers | - | Middlesbrough FC | 2:0 | ||||
| Championship | 14/04/15 | Middlesbrough FC | - | Wolverhampton Wanderers | 2:1 |  |
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| Championship | 24/10/15 | Wolverhampton Wanderers | - | Middlesbrough FC | 1:3 |  |
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| Championship | 05/08/17 | Wolverhampton Wanderers | - | Middlesbrough FC | 1:0 | ||||
| Championship | 10/02/18 | Middlesbrough FC | - | Reading FC | 2:1 | ||||
| League Cup | 04/09/20 | Middlesbrough FC | - | Shrewsbury Town | 4:3 |
England