Home History
| Inglaterra - Premier League Cup sub-21 | 2024/02/20 19:00 | Fulham sub-21 v Middlesbrough sub-21 | L | 2-1 |
| Inglaterra - Premier League 2 | 2024/02/16 19:00 | Aston Villa sub-21 v Middlesbrough sub-21 | L | 4-0 |
| Inglaterra - Premier League Cup sub-21 | 2024/02/05 19:00 | Birmingham sub-21 v Middlesbrough sub-21 | W | 0-4 |
| Inglaterra - Premier League 2 | 2024/01/26 19:00 | Middlesbrough sub-21 v West Brom sub-21 | L | 0-1 |
| Inglaterra - Premier League Cup sub-21 | 2024/01/23 19:00 | Ipswich sub-21 v Middlesbrough sub-21 | L | 2-0 |
| Inglaterra - Premier League 2 | 2024/01/12 19:00 | Arsenal sub-21 v Middlesbrough sub-21 | L | 1-0 |
| Inglaterra - Premier League 2 | 2023/12/18 19:00 | Reading sub-21 v Middlesbrough sub-21 | D | 2-2 |
| Inglaterra - Premier League Cup sub-21 | 2023/12/11 19:00 | Crystal Palace sub-21 v Middlesbrough sub-21 | W | 0-4 |
Away History
| Inglaterra - Premier League 2 | 2024/02/19 12:00 | Leeds sub-21 v Chelsea sub-21 | W | 0-2 |
| Premier League International Cup | 2024/02/15 19:00 | Chelsea sub-21 v PSV sub-21 | L | 1-2 |
| Inglaterra - Premier League 2 | 2024/02/09 19:00 | West Ham United sub-21 v Chelsea sub-21 | W | 0-2 |
| Inglaterra - Premier League Cup sub-21 | 2024/02/02 19:00 | Chelsea sub-21 v Leeds sub-21 | D | 3-3 |
| Inglaterra - Premier League 2 | 2024/01/27 14:00 | Chelsea sub-21 v Reading sub-21 | W | 3-2 |
| Inglaterra - Premier League Cup sub-21 | 2024/01/22 19:00 | Chelsea sub-21 v Colchester sub-21 | W | 4-1 |
| Inglaterra - Premier League 2 | 2024/01/12 19:00 | Chelsea sub-21 v Manchester United sub-21 | W | 3-2 |
| Premier League International Cup | 2024/01/09 19:00 | Chelsea sub-21 v Valencia sub-21 | D | 1-1 |