Head to Head
| England Premier League 2 | 2021/08/16 18:00 | Wolverhampton U23 v Middlesbrough U23 | L | 2-1 |
| England Premier League 2 | 2021/03/22 12:00 | Middlesbrough U23 v Wolverhampton U23 | D | 1-1 |
| England Premier League 2 | 2020/11/20 13:30 | Wolverhampton U23 v Middlesbrough U23 | W | 1-4 |
| England Premier League 2 | 2019/03/01 19:00 | Middlesbrough U23 v Wolverhampton U23 | D | 0-0 |
| England Premier League 2 | 2018/09/28 18:00 | Wolverhampton U23 v Middlesbrough U23 | L | 2-0 |
| England Premier League 2 | 2018/04/12 14:00 | Wolverhampton U23 v Middlesbrough U23 | D | 1-1 |
| England Premier League 2 | 2017/10/29 13:00 | Middlesbrough U23 v Wolverhampton U23 | W | 3-1 |
| England Premier League 2 | 2017/04/17 12:00 | Middlesbrough U23 v Wolverhampton U23 | L | 0-1 |
| England Premier League 2 | 2016/09/19 18:00 | Wolverhampton U23 v Middlesbrough U23 | L | 2-1 |