Home History
| 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 |
| 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 |
Away History
| Anglia - Premier League 2 | 2023/09/01 18:00 | Wolverhampton U21 v Crystal Palace U21 | L | 3-2 |
| Anglia - Premier League 2 | 2023/08/28 12:00 | Crystal Palace U21 v Fulham U21 | L | 2-5 |
| Anglia - Premier League 2 | 2023/08/20 12:00 | Reading U21 v Crystal Palace U21 | L | 2-0 |
| Anglia - Premier League 2 | 2023/08/14 12:00 | Crystal Palace U21 v Man Utd U21 | W | 3-2 |
| Premier League International Cup | 2023/05/23 18:00 | Crystal Palace U21 v PSV U21 | L | 1-3 |
| Anglia - Premier League 2 | 2023/05/06 12:00 | Crystal Palace U21 v Liverpool U21 | L | 0-1 |
| Premier League International Cup | 2023/05/03 18:00 | Crystal Palace U21 v Valencia U21 | W | 6-4 |
| Anglia - Premier League 2 | 2023/04/28 10:00 | Crystal Palace U21 v Blackburn U21 | L | 0-3 |
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