Home History
| England Premier League 2 | 2024/05/04 11:00 | Reading U21 v Middlesbrough U21 | L | 2-0 |
| England Premier League 2 | 2024/04/26 18:00 | Middlesbrough U21 v Crystal Palace U21 | L | 2-3 |
| England Premier League 2 | 2024/04/15 18:00 | Sunderland U21 v Middlesbrough U21 | W | 1-2 |
| England Premier League 2 | 2024/04/08 11:00 | Fulham U21 v Middlesbrough U21 | D | 2-2 |
| England Premier League 2 | 2024/03/22 19:00 | Middlesbrough U21 v Newcastle U21 | W | 3-2 |
| England Premier League 2 | 2024/03/17 13:00 | Middlesbrough U21 v Tottenham U21 | L | 1-2 |
| England Premier League 2 | 2024/03/08 19:00 | Middlesbrough U21 v Man Utd U21 | W | 3-2 |
| England Premier League 2 | 2024/03/01 19:00 | Norwich U21 v Middlesbrough U21 | W | 2-3 |
Away History
| 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 |