Head to Head
| England Premier League 2 | 2023/08/25 18:00 | Middlesbrough U21 v Wolverhampton U21 | W | 3-2 |
Home History
| England National League Cup | 2025/09/09 18:00 | Halifax v Middlesbrough U21 | L | 2-1 |
| England Premier League 2 | 2025/08/29 18:00 | Middlesbrough U21 v Reading U21 | W | 5-2 |
| England Premier League 2 | 2025/08/18 18:00 | Middlesbrough U21 v Man Utd U21 | L | 0-1 |
| England National League Cup | 2025/08/09 12:00 | Boston Utd v Middlesbrough U21 | L | 2-1 |
| England Premier League 2 | 2025/04/18 18:00 | Middlesbrough U21 v West Brom U21 | W | 2-1 |
| England Premier League 2 | 2025/04/11 18:00 | Middlesbrough U21 v West Ham U21 | D | 1-1 |
| England Premier League 2 | 2025/04/04 18:00 | Leeds U21 v Middlesbrough U21 | W | 0-2 |
| England Premier League 2 | 2025/03/16 13:00 | Middlesbrough U21 v Southampton U21 | W | 1-0 |
Away History
| Premier League International Cup | 2025/09/10 18:00 | Wolverhampton U21 v Real Madrid U21 | L | 0-1 |
| England EFL Trophy | 2025/09/02 18:00 | Stockport v Wolverhampton U21 | L | 5-3 |
| England Premier League 2 | 2025/08/29 18:00 | Wolverhampton U21 v Blackburn U21 | W | 3-1 |
| England Premier League 2 | 2025/08/22 18:00 | Wolverhampton U21 v Stoke U21 | D | 2-2 |
| England Premier League 2 | 2025/08/18 18:00 | Burnley U21 v Wolverhampton U21 | W | 1-2 |
| England National League Cup | 2025/08/12 18:00 | Wealdstone v Wolverhampton U21 | L | 2-1 |
| England Premier League 2 | 2025/04/26 17:00 | Chelsea U21 v Wolverhampton U21 | L | 4-0 |
| England Premier League 2 | 2025/04/14 18:00 | Wolverhampton U21 v Man Utd U21 | D | 1-1 |