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