Head to Head
| Anglia - Premier League 2 | 2023/03/24 14:00 | Derby U21 v Middlesbrough U21 | W | 1-5 |
| Anglia - Premier League 2 | 2022/08/12 17:00 | Middlesbrough U21 v Derby U21 | W | 3-1 |
Home History
| Anglia - Premier League 2 | 2023/10/27 18:00 | West Ham U21 v Middlesbrough U21 | L | 5-0 |
| Anglia - Premier League Cup U21 | 2023/10/06 18:00 | Middlesbrough U21 v Ipswich U21 | W | 2-0 |
| Anglia - Premier League 2 | 2023/09/29 18:00 | Middlesbrough U21 v Stoke U21 | W | 4-1 |
| Anglia - Premier League 2 | 2023/09/25 18:00 | Leicester U21 v Middlesbrough U21 | W | 1-3 |
| Anglia - Premier League Cup U21 | 2023/09/15 18:00 | Middlesbrough U21 v Crystal Palace U21 | L | 2-6 |
| Anglia - Premier League 2 | 2023/09/03 13:00 | Liverpool U21 v Middlesbrough U21 | W | 1-4 |
| Anglia - Premier League 2 | 2023/08/25 18:00 | Middlesbrough U21 v Wolverhampton U21 | W | 3-2 |
| Anglia - Premier League 2 | 2023/08/18 18:00 | Middlesbrough U21 v Everton U21 | D | 2-2 |
Away History
| Anglia - Premier League 2 | 2023/10/28 11:00 | Derby U21 v Man City U21 | W | 4-2 |
| Anglia - Premier League 2 | 2023/09/29 18:00 | Derby U21 v Brighton U21 | L | 2-3 |
| Anglia - Premier League 2 | 2023/09/25 18:00 | Sunderland U21 v Derby U21 | L | 3-1 |
| Anglia - Premier League 2 | 2023/09/01 17:00 | Aston Villa U21 v Derby U21 | L | 3-1 |
| Anglia - Premier League 2 | 2023/08/25 18:00 | Derby U21 v Tottenham U21 | L | 0-2 |
| Anglia - Premier League 2 | 2023/08/18 18:00 | Derby U21 v Liverpool U21 | D | 1-1 |
| Anglia - Premier League 2 | 2023/08/14 18:00 | Leicester U21 v Derby U21 | L | 2-1 |
| Anglia - Premier League 2 | 2023/04/24 18:00 | Derby U21 v Newcastle U21 | L | 1-4 |