Home History
| England Premier League 2 | 2023/08/18 18:00 | Middlesbrough U21 v Everton U21 | D | 2-2 |
| England Premier League 2 | 2023/08/14 18:00 | Nottm Forest U21 v Middlesbrough U21 | D | 2-2 |
| England Premier League 2 | 2023/04/23 13:00 | Leeds U21 v Middlesbrough U21 | L | 3-1 |
| England Premier League 2 | 2023/04/14 18:00 | Middlesbrough U21 v Nottm Forest U21 | L | 0-1 |
| England Premier League 2 | 2023/04/03 18:00 | Newcastle U21 v Middlesbrough U21 | D | 0-0 |
| England Premier League 2 | 2023/03/24 14:00 | Derby U21 v Middlesbrough U21 | W | 1-5 |
| England Premier League 2 | 2023/03/06 19:00 | Middlesbrough U21 v Aston Villa U21 | L | 2-3 |
| England Premier League 2 | 2023/02/24 12:00 | Norwich U21 v Middlesbrough U21 | D | 2-2 |
Away History
| England Premier League 2 | 2023/08/21 18:00 | Stoke U21 v Wolverhampton U21 | L | 2-1 |
| England Premier League 2 | 2023/08/11 18:00 | Wolverhampton U21 v Fulham U21 | L | 2-3 |
| England Premier League 2 | 2023/04/29 12:00 | Man City U21 v Wolverhampton U21 | L | 4-3 |
| England Premier League 2 | 2023/04/24 18:00 | Wolverhampton U21 v Crystal Palace U21 | W | 5-0 |
| England Premier League 2 | 2023/04/17 18:00 | Fulham U21 v Wolverhampton U21 | L | 2-1 |
| England Premier League 2 | 2023/04/10 18:00 | Wolverhampton U21 v Everton U21 | W | 5-0 |
| England Premier League 2 | 2023/04/07 12:00 | Tottenham U21 v Wolverhampton U21 | D | 1-1 |
| England Premier League 2 | 2023/03/31 18:00 | Everton U21 v Wolverhampton U21 | L | 3-0 |