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 | 2020/03/02 19:00 | Tottenham U23 v Wolverhampton U23 | L | 3-2 |
| England U23 Premier League Cup | 2020/02/25 14:01 | Wolverhampton U23 v Derby U23 | L | 1-3 |
| England U23 Premier League Cup | 2020/02/21 19:00 | Leeds U23 v Wolverhampton U23 | D | 1-1 |
| England Premier League 2 | 2020/02/17 19:00 | Wolverhampton U23 v Liverpool U23 | L | 1-2 |
| England U23 Premier League Cup | 2020/02/06 14:00 | Birmingham U23 v Wolverhampton U23 | D | 2-2 |
| England Premier League 2 | 2020/02/03 19:00 | Southampton U23 v Wolverhampton U23 | L | 1-0 |
| Youth Tournament | 2020/01/29 18:59 | Wolverhampton U23 v Liverpool U23 | D | 2-2 |
| England U23 Premier League Cup | 2020/01/24 13:00 | Wolverhampton U23 v Leeds U23 | D | 2-2 |
Away History
| England U23 Premier League Cup | 2020/03/07 12:30 | Derby U23 v Middlesbrough U23 | L | 6-0 |
| England Premier League 2 | 2020/02/28 19:00 | Middlesbrough U23 v Newcastle U23 | L | 0-2 |
| England U23 Premier League Cup | 2020/02/21 19:00 | Middlesbrough U23 v Crystal Palace U23 | D | 1-1 |
| England Premier League 2 | 2020/02/17 19:00 | Reading U23 v Middlesbrough U23 | W | 0-1 |
| England U23 Premier League Cup | 2020/02/07 19:00 | Middlesbrough U23 v Blackburn U23 | W | 4-1 |
| England Premier League 2 | 2020/02/02 13:00 | Middlesbrough U23 v Fulham U23 | W | 1-0 |
| England U23 Premier League Cup | 2020/01/20 13:00 | Burnley U23 v Middlesbrough U23 | W | 1-2 |
| England Premier League 2 | 2020/01/13 13:00 | Swansea U23 v Middlesbrough U23 | L | 5-1 |