Home History
| Anglia - Premier League Cup - U21 | 2024/02/20 19:00 | Fulham - U21 v Middlesbrough - U21 | L | 2-1 |
| Anglia - Premier League 2 | 2024/02/16 19:00 | Aston Villa - U21 v Middlesbrough - U21 | L | 4-0 |
| Anglia - Premier League Cup - U21 | 2024/02/05 19:00 | Birmingham - U21 v Middlesbrough - U21 | W | 0-4 |
| Anglia - Premier League 2 | 2024/01/26 19:00 | Middlesbrough - U21 v West Brom - U21 | L | 0-1 |
| Anglia - Premier League Cup - U21 | 2024/01/23 19:00 | Ipswich - U21 v Middlesbrough - U21 | L | 2-0 |
| Anglia - Premier League 2 | 2024/01/12 19:00 | Arsenal - U21 v Middlesbrough - U21 | L | 1-0 |
| Anglia - Premier League 2 | 2023/12/18 19:00 | Reading - U21 v Middlesbrough - U21 | D | 2-2 |
| Anglia - Premier League Cup - U21 | 2023/12/11 19:00 | Crystal Palace - U21 v Middlesbrough - U21 | W | 0-4 |
Away History
| Anglia - Premier League 2 | 2024/02/19 12:00 | Leeds - U21 v Chelsea - U21 | W | 0-2 |
| Premier League International Cup | 2024/02/15 19:00 | Chelsea - U21 v PSV - U21 | L | 1-2 |
| Anglia - Premier League 2 | 2024/02/09 19:00 | West Ham - U21 v Chelsea - U21 | W | 0-2 |
| Anglia - Premier League Cup - U21 | 2024/02/02 19:00 | Chelsea - U21 v Leeds - U21 | D | 3-3 |
| Anglia - Premier League 2 | 2024/01/27 14:00 | Chelsea - U21 v Reading - U21 | W | 3-2 |
| Anglia - Premier League Cup - U21 | 2024/01/22 19:00 | Chelsea - U21 v Colchester - U21 | W | 4-1 |
| Anglia - Premier League 2 | 2024/01/12 19:00 | Chelsea - U21 v Manchester Utd - U21 | W | 3-2 |
| Premier League International Cup | 2024/01/09 19:00 | Chelsea - U21 v Valencia - U21 | D | 1-1 |