Home History
| 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 |
| 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 |
Away History
| Anglia - Development League 2 | 2023/10/03 12:00 | Ipswich U21 v Cardiff U21 | W | 5-2 |
| Anglia - Development League 2 | 2023/09/25 12:00 | Bristol City U21 v Ipswich U21 | L | 2-0 |
| Anglia - Premier League Cup U21 | 2023/09/18 18:00 | Ipswich U21 v Birmingham U21 | D | 0-0 |
| Anglia - Development League 2 | 2023/09/12 12:00 | Barnsley U21 v Ipswich U21 | W | 1-3 |
| Anglia - Development League 2 | 2023/09/05 12:00 | Ipswich U21 v Coventry U21 | W | 3-0 |
| Anglia - Development League 2 | 2023/08/29 12:00 | Fleetwood Town U21 v Ipswich U21 | L | 1-0 |
| Anglia - Development League 2 | 2023/08/22 12:30 | Ipswich U21 v Birmingham U21 | L | 1-2 |
| Anglia - Development League 2 | 2023/08/15 13:00 | Sheff Utd U21 v Ipswich U21 | L | 6-0 |