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