Home History
| 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 |
| England Premier League 2 | 2023/09/03 13:00 | Liverpool U21 v Middlesbrough U21 | W | 1-4 |
Away History
| Europe Friendlies | 2023/11/28 18:00 | Chelsea U21 v Strasbourg II | L | 1-4 |
| England U21 Premier League Cup | 2023/11/12 13:00 | Leeds U21 v Chelsea U21 | W | 1-2 |
| England EFL Trophy | 2023/11/07 19:00 | Oxford Utd v Chelsea U21 | L | 5-0 |
| England Premier League 2 | 2023/11/03 19:00 | Chelsea U21 v Fulham U21 | D | 2-2 |
| Premier League International Cup | 2023/10/31 19:00 | Chelsea U21 v Dinamo Zagreb U21 | W | 4-1 |
| England Premier League 2 | 2023/10/27 18:00 | Chelsea U21 v Leicester U21 | D | 1-1 |
| England U21 Premier League Cup | 2023/10/06 18:00 | Colchester U21 v Chelsea U21 | W | 2-5 |
| England Premier League 2 | 2023/10/02 18:00 | Tottenham U21 v Chelsea U21 | L | 4-2 |