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 | 2025/11/07 13:00 | Middlesbrough U21 v Norwich U21 | D | 2-2 |
| England Premier League 2 | 2025/11/01 14:00 | Liverpool U21 v Middlesbrough U21 | L | 4-2 |
| England National League Cup | 2025/10/28 19:00 | Scunthorpe v Middlesbrough U21 | L | 3-2 |
| England Premier League 2 | 2025/10/24 18:00 | Middlesbrough U21 v Wolverhampton U21 | L | 0-1 |
| England Premier League 2 | 2025/10/04 15:00 | Brighton U21 v Middlesbrough U21 | D | 1-1 |
| England Premier League 2 | 2025/09/26 18:00 | Middlesbrough U21 v Everton U21 | L | 0-1 |
| England Premier League 2 | 2025/09/22 18:00 | Blackburn U21 v Middlesbrough U21 | D | 1-1 |
| England National League Cup | 2025/09/17 18:30 | Gateshead v Middlesbrough U21 | W | 0-2 |
Away History
| England U21 Premier League Cup | 2025/12/01 19:00 | Ipswich U21 v Leicester U21 | W | 1-0 |
| England U21 Premier League Cup | 2025/11/21 19:00 | Leicester U21 v Ipswich U21 | W | 0-2 |
| England U21 Premier League Cup | 2025/11/18 19:00 | Charlton U21 v Ipswich U21 | L | 2-1 |
| England Premier League 2 | 2025/11/07 19:00 | Sunderland U21 v Ipswich U21 | L | 4-2 |
| England Premier League 2 | 2025/10/31 19:00 | Ipswich U21 v Newcastle U21 | W | 1-0 |
| England U21 Premier League Cup | 2025/10/28 19:00 | Ipswich U21 v Preston U21 | D | 2-2 |
| England Premier League 2 | 2025/10/24 18:00 | Ipswich U21 v Brighton U21 | W | 3-1 |
| England Premier League 2 | 2025/10/03 18:00 | Nottm Forest U21 v Ipswich U21 | W | 0-1 |