Home History
| Angleterre - Premier League Cup - U21 | 2023/11/12 12:00 | Middlesbrough - U21 v Birmingham - U21 | L | 0-2 |
| Angleterre - Premier League 2 | 2023/11/05 13:00 | Middlesbrough - U21 v Derby - U21 | W | 1-0 |
| Angleterre - Premier League 2 | 2023/10/27 18:00 | West Ham - U21 v Middlesbrough - U21 | L | 5-0 |
| Angleterre - Premier League Cup - U21 | 2023/10/06 18:00 | Middlesbrough - U21 v Ipswich - U21 | W | 2-0 |
| Angleterre - Premier League 2 | 2023/09/29 18:00 | Middlesbrough - U21 v Stoke - U21 | W | 4-1 |
| Angleterre - Premier League 2 | 2023/09/25 18:00 | Leicester - U21 v Middlesbrough - U21 | W | 1-3 |
| Angleterre - Premier League Cup - U21 | 2023/09/15 18:00 | Middlesbrough - U21 v Crystal Palace - U21 | L | 2-6 |
| Angleterre - Premier League 2 | 2023/09/03 13:00 | Liverpool - U21 v Middlesbrough - U21 | W | 1-4 |
Away History
| Europe - Matchs amicaux | 2023/11/28 18:00 | Chelsea - U21 v Strasbourg II | L | 1-4 |
| Angleterre - Premier League Cup - U21 | 2023/11/12 13:00 | Leeds - U21 v Chelsea - U21 | W | 1-2 |
| Angleterre - EFL Trophy | 2023/11/07 19:00 | Oxford Utd v Chelsea - U21 | L | 5-0 |
| Angleterre - 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 |
| Angleterre - Premier League 2 | 2023/10/27 18:00 | Chelsea - U21 v Leicester - U21 | D | 1-1 |
| Angleterre - Premier League Cup - U21 | 2023/10/06 18:00 | Colchester - U21 v Chelsea - U21 | W | 2-5 |
| Angleterre - Premier League 2 | 2023/10/02 18:00 | Tottenham - U21 v Chelsea - U21 | L | 4-2 |
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