Head to Head
| 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 | W | 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 | L | 3-1 |
| England - Premier League 2 | 2017/04/17 12:00 | Middlesbrough U23 v Wolverhampton U23 | W | 0-1 |
| England - Premier League 2 | 2016/09/19 18:00 | Wolverhampton U23 v Middlesbrough U23 | W | 2-1 |
Home History
| England - Premier League 2 | 2020/11/06 13:00 | Sunderland U23 v Wolverhampton U23 | L | 2-1 |
| England - Premier League 2 | 2020/11/02 14:00 | Wolverhampton U23 v Fulham U23 | W | 3-0 |
| England - Premier League 2 | 2020/10/26 14:00 | Crystal Palace U23 v Wolverhampton U23 | L | 2-1 |
| England - Premier League 2 | 2020/10/19 12:00 | Wolverhampton U23 v Aston Villa U23 | L | 1-3 |
| England - Premier League 2 | 2020/09/28 13:00 | Wolverhampton U23 v Stoke U23 | W | 3-0 |
| England - Premier League 2 | 2020/09/18 13:00 | Leeds U23 v Wolverhampton U23 | D | 2-2 |
| England - Premier League 2 | 2020/09/12 11:00 | Wolverhampton U23 v Burnley U23 | W | 3-2 |
| England - Premier League 2 | 2020/03/02 19:00 | Tottenham U23 v Wolverhampton U23 | L | 3-2 |
Away History
| England - Premier League 2 | 2020/11/08 14:00 | Middlesbrough U23 v West Brom U23 | L | 0-1 |
| England - Premier League 2 | 2020/10/30 13:00 | Norwich U23 v Middlesbrough U23 | W | 1-3 |
| England - Premier League 2 | 2020/10/23 13:00 | Middlesbrough U23 v Burnley U23 | W | 3-0 |
| England - Premier League 2 | 2020/10/19 12:00 | Sunderland U23 v Middlesbrough U23 | W | 0-6 |
| England - Premier League 2 | 2020/10/02 12:00 | Leeds U23 v Middlesbrough U23 | L | 1-0 |
| England - Premier League 2 | 2020/09/21 14:00 | Middlesbrough U23 v Stoke U23 | W | 2-0 |
| England - Premier League 2 | 2020/09/11 11:00 | Newcastle U23 v Middlesbrough U23 | D | 2-2 |
| England - Premier League Cup - U23 | 2020/03/07 12:30 | Derby U23 v Middlesbrough U23 | L | 6-0 |