Head to Head
| Anglia - Premier League 2 | 2021/03/22 12:00 | Middlesbrough - U23 v Wolverhampton - U23 | D | 1-1 |
| Anglia - Premier League 2 | 2020/11/20 13:30 | Wolverhampton - U23 v Middlesbrough - U23 | L | 1-4 |
| Anglia - Premier League 2 | 2019/03/01 19:00 | Middlesbrough - U23 v Wolverhampton - U23 | D | 0-0 |
| Anglia - Premier League 2 | 2018/09/28 18:00 | Wolverhampton - U23 v Middlesbrough - U23 | W | 2-0 |
| Anglia - Premier League 2 | 2018/04/12 14:00 | Wolverhampton - U23 v Middlesbrough - U23 | D | 1-1 |
| Anglia - Premier League 2 | 2017/10/29 13:00 | Middlesbrough - U23 v Wolverhampton - U23 | L | 3-1 |
| Anglia - Premier League 2 | 2017/04/17 12:00 | Middlesbrough - U23 v Wolverhampton - U23 | W | 0-1 |
| Anglia - Premier League 2 | 2016/09/19 18:00 | Wolverhampton - U23 v Middlesbrough - U23 | W | 2-1 |
Home History
| Anglia - Premier League 2 | 2021/05/17 18:00 | Crystal Palace - U23 v Wolverhampton - U23 | L | 3-2 |
| Anglia - Premier League 2 | 2021/05/10 12:00 | Wolverhampton - U23 v Reading - U23 | D | 2-2 |
| Anglia - Premier League 2 | 2021/04/30 12:00 | Reading - U23 v Wolverhampton - U23 | L | 5-0 |
| Anglia - Premier League 2 | 2021/04/26 12:00 | Wolverhampton - U23 v Norwich - U23 | W | 3-0 |
| Anglia - Premier League 2 | 2021/04/19 11:00 | Wolverhampton - U23 v West Brom - U23 | D | 1-1 |
| Anglia - Premier League 2 | 2021/04/12 11:00 | Wolverhampton - U23 v Newcastle - U23 | W | 4-0 |
| Anglia - Premier League 2 | 2021/04/02 14:00 | Aston Villa - U23 v Wolverhampton - U23 | L | 4-0 |
| Anglia - Premier League 2 | 2021/03/22 12:00 | Middlesbrough - U23 v Wolverhampton - U23 | D | 1-1 |
Away History
| Anglia - Premier League 2 | 2021/05/07 12:00 | Middlesbrough - U23 v Crystal Palace - U23 | L | 0-1 |
| Anglia - Premier League 2 | 2021/05/03 12:00 | Crystal Palace - U23 v Middlesbrough - U23 | L | 3-2 |
| Anglia - Premier League 2 | 2021/04/23 14:00 | Middlesbrough - U23 v Aston Villa - U23 | W | 4-1 |
| Anglia - Premier League 2 | 2021/04/16 13:00 | Middlesbrough - U23 v Fulham - U23 | W | 1-0 |
| Anglia - Premier League 2 | 2021/04/09 12:00 | Reading - U23 v Middlesbrough - U23 | W | 2-4 |
| Anglia - Premier League 2 | 2021/03/22 12:00 | Middlesbrough - U23 v Wolverhampton - U23 | D | 1-1 |
| Anglia - Premier League 2 | 2021/03/12 13:00 | West Brom - U23 v Middlesbrough - U23 | W | 0-1 |
| Anglia - Premier League 2 | 2021/03/05 14:00 | Middlesbrough - U23 v Newcastle - U23 | W | 2-1 |