Home History
| Inglaterra - Taça da Premier League de Sub21 | 2023/11/12 12:00 | Middlesbrough Sub21 v Birmingham Sub21 | L | 0-2 |
| Inglaterra - Premier League 2 | 2023/11/05 13:00 | Middlesbrough Sub21 v Derby Sub21 | W | 1-0 |
| Inglaterra - Premier League 2 | 2023/10/27 18:00 | West Ham Sub21 v Middlesbrough Sub21 | L | 5-0 |
| Inglaterra - Taça da Premier League de Sub21 | 2023/10/06 18:00 | Middlesbrough Sub21 v Ipswich Sub21 | W | 2-0 |
| Inglaterra - Premier League 2 | 2023/09/29 18:00 | Middlesbrough Sub21 v Stoke Sub21 | W | 4-1 |
| Inglaterra - Premier League 2 | 2023/09/25 18:00 | Leicester Sub21 v Middlesbrough Sub21 | W | 1-3 |
| Inglaterra - Taça da Premier League de Sub21 | 2023/09/15 18:00 | Middlesbrough Sub21 v Crystal Palace Sub21 | L | 2-6 |
| Inglaterra - Premier League 2 | 2023/09/03 13:00 | Liverpool Sub21 v Middlesbrough Sub21 | W | 1-4 |
Away History
| Europa - Amigáveis | 2023/11/28 18:00 | Chelsea Sub21 v Strasbourg II | L | 1-4 |
| Inglaterra - Taça da Premier League de Sub21 | 2023/11/12 13:00 | Leeds Sub21 v Chelsea Sub21 | W | 1-2 |
| Inglaterra - EFL Trophy | 2023/11/07 19:00 | Oxford Utd v Chelsea Sub21 | L | 5-0 |
| Inglaterra - Premier League 2 | 2023/11/03 19:00 | Chelsea Sub21 v Fulham Sub21 | D | 2-2 |
| Premier League International Cup | 2023/10/31 19:00 | Chelsea Sub21 v Dinamo Zagreb Sub21 | W | 4-1 |
| Inglaterra - Premier League 2 | 2023/10/27 18:00 | Chelsea Sub21 v Leicester Sub21 | D | 1-1 |
| Inglaterra - Taça da Premier League de Sub21 | 2023/10/06 18:00 | Colchester Sub21 v Chelsea Sub21 | W | 2-5 |
| Inglaterra - Premier League 2 | 2023/10/02 18:00 | Tottenham Sub21 v Chelsea Sub21 | L | 4-2 |
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