Head to Head
| England U21 Premier League Cup | 2023/10/06 18:00 | Middlesbrough U21 v Ipswich U21 | L | 2-0 |
Home History
| England U21 Premier League Cup | 2023/12/08 19:00 | Birmingham U21 v Ipswich U21 | L | 4-2 |
| England Development League 2 | 2023/12/05 19:00 | Bournemouth U21 v Ipswich U21 | W | 1-3 |
| England Development League 2 | 2023/11/28 12:00 | Swansea U21 v Ipswich U21 | L | 4-0 |
| England Development League 2 | 2023/11/21 13:00 | Ipswich U21 v Millwall U21 | D | 1-1 |
| England U21 Premier League Cup | 2023/11/10 19:00 | Crystal Palace U21 v Ipswich U21 | W | 2-4 |
| England Development League 2 | 2023/11/06 13:00 | Charlton U21 v Ipswich U21 | L | 5-0 |
| England Development League 2 | 2023/10/31 19:00 | Ipswich U21 v Colchester U21 | W | 2-0 |
| England Development League 2 | 2023/10/23 12:00 | QPR U21 v Ipswich U21 | D | 1-1 |
Away History
| England U21 Premier League Cup | 2023/12/11 19:00 | Crystal Palace U21 v Middlesbrough U21 | W | 0-4 |
| England U21 Premier League Cup | 2023/11/12 12:00 | Middlesbrough U21 v Birmingham U21 | L | 0-2 |
| England Premier League 2 | 2023/11/05 13:00 | Middlesbrough U21 v Derby U21 | W | 1-0 |
| England Premier League 2 | 2023/10/27 18:00 | West Ham U21 v Middlesbrough U21 | L | 5-0 |
| England U21 Premier League Cup | 2023/10/06 18:00 | Middlesbrough U21 v Ipswich U21 | W | 2-0 |
| England Premier League 2 | 2023/09/29 18:00 | Middlesbrough U21 v Stoke U21 | W | 4-1 |
| England Premier League 2 | 2023/09/25 18:00 | Leicester U21 v Middlesbrough U21 | W | 1-3 |
| England U21 Premier League Cup | 2023/09/15 18:00 | Middlesbrough U21 v Crystal Palace U21 | L | 2-6 |