Home History
| England Premier League 2 | 2024/12/13 19:00 | Norwich U21 v Middlesbrough U21 | W | 1-3 |
| England Premier League 2 | 2024/11/29 12:00 | Tottenham U21 v Middlesbrough U21 | L | 6-1 |
| England National League Cup | 2024/11/12 19:00 | Halifax v Middlesbrough U21 | W | 1-4 |
| Premier League International Cup | 2024/11/06 19:00 | Middlesbrough U21 v Borussia M'gladbach U21 | W | 3-2 |
| England Premier League 2 | 2024/11/02 15:00 | Middlesbrough U21 v Nottm Forest U21 | L | 1-4 |
| Premier League International Cup | 2024/10/30 19:00 | Middlesbrough U21 v Lyon U21 | L | 0-1 |
| England Premier League 2 | 2024/10/25 18:00 | Middlesbrough U21 v Aston Villa U21 | W | 4-2 |
| England Premier League 2 | 2024/10/04 18:00 | Stoke U21 v Middlesbrough U21 | W | 1-3 |
Away History
| Premier League International Cup | 2024/10/17 18:00 | Blackburn U21 v Benfica U21 | D | 1-1 |
| Premier League International Cup | 2024/09/24 18:00 | West Ham U21 v Benfica U21 | D | 2-2 |
| Premier League International Cup | 2024/01/24 19:00 | Everton U21 v Benfica U21 | L | 2-1 |
| Premier League International Cup | 2024/01/08 19:00 | Fulham U21 v Benfica U21 | L | 3-1 |
| Premier League International Cup | 2023/12/06 19:00 | Crystal Palace U21 v Benfica U21 | L | 2-1 |
| Premier League International Cup | 2023/10/22 13:00 | Liverpool U21 v Benfica U21 | D | 1-1 |