Head to Head
| England U21 Premier League Cup | 2024/01/23 19:00 | Ipswich U21 v Middlesbrough U21 | L | 2-0 |
| England U21 Premier League Cup | 2023/10/06 18:00 | Middlesbrough U21 v Ipswich U21 | W | 2-0 |
Home History
| England Premier League 2 | 2025/08/29 18:00 | Middlesbrough U21 v Reading U21 | W | 5-2 |
| England Premier League 2 | 2025/08/18 18:00 | Middlesbrough U21 v Man Utd U21 | L | 0-1 |
| England National League Cup | 2025/08/09 12:00 | Boston Utd v Middlesbrough U21 | L | 2-1 |
| England Premier League 2 | 2025/04/18 18:00 | Middlesbrough U21 v West Brom U21 | W | 2-1 |
| England Premier League 2 | 2025/04/11 18:00 | Middlesbrough U21 v West Ham U21 | D | 1-1 |
| England Premier League 2 | 2025/04/04 18:00 | Leeds U21 v Middlesbrough U21 | W | 0-2 |
| England Premier League 2 | 2025/03/16 13:00 | Middlesbrough U21 v Southampton U21 | W | 1-0 |
| England Premier League 2 | 2025/03/07 19:00 | Middlesbrough U21 v Newcastle U21 | L | 0-2 |
Away History
| England Premier League 2 | 2025/08/29 18:00 | Ipswich U21 v Southampton U21 | D | 2-2 |
| England Development League 2 | 2025/08/24 12:00 | Leeds U21 v Ipswich U21 | W | 2-3 |
| England Premier League 2 | 2025/08/15 18:00 | Ipswich U21 v Derby U21 | W | 4-3 |
| England Development League 2 | 2025/05/06 10:00 | Ipswich U21 v Fleetwood Town U21 | L | 1-2 |
| England Development League 2 | 2025/04/28 11:00 | Sheffield Wed U21 v Ipswich U21 | W | 1-3 |
| England Development League 2 | 2025/04/21 12:00 | Bournemouth U21 v Ipswich U21 | L | 7-0 |
| England Development League 2 | 2025/04/11 18:00 | Ipswich U21 v Coventry U21 | W | 4-1 |
| England Development League 2 | 2025/04/08 12:30 | Peterborough U21 v Ipswich U21 | W | 2-3 |