Head to Head
| England - Premier League 2 | 2018/12/07 19:00 | Man Utd U23 v Middlesbrough U23 | L | 2-0 |
| England - Premier League 2 | 2018/09/23 12:00 | Middlesbrough U23 v Man Utd U23 | L | 0-2 |
Home History
| England - Premier League 2 | 2019/10/28 19:00 | Newcastle U23 v Middlesbrough U23 | D | 2-2 |
| England - Premier League 2 | 2019/10/18 18:00 | Middlesbrough U23 v Reading U23 | W | 2-1 |
| England - U23 Premier League Cup | 2019/10/06 11:59 | Middlesbrough U23 v Burnley U23 | D | 1-1 |
| England - Premier League 2 | 2019/09/27 11:00 | Fulham U23 v Middlesbrough U23 | W | 2-4 |
| England - Premier League 2 | 2019/09/20 18:00 | Middlesbrough U23 v West Ham U23 | L | 3-4 |
| England - Premier League 2 | 2019/09/16 18:00 | Sunderland U23 v Middlesbrough U23 | W | 2-3 |
| England - Premier League 2 | 2019/08/30 18:00 | Norwich U23 v Middlesbrough U23 | D | 2-2 |
| England - Premier League 2 | 2019/08/23 12:00 | Middlesbrough U23 v Swansea U23 | W | 3-2 |
Away History
| England - Premier League 2 | 2019/10/25 18:00 | Man Utd U23 v Stoke U23 | W | 3-1 |
| England - Premier League 2 | 2019/10/21 18:00 | Swansea U23 v Man Utd U23 | W | 1-4 |
| England - Premier League 2 | 2019/09/27 18:00 | Man Utd U23 v Norwich U23 | W | 2-0 |
| England - Premier League 2 | 2019/09/23 18:00 | Aston Villa U23 v Man Utd U23 | L | 4-1 |
| England - Premier League 2 | 2019/09/13 18:00 | Man Utd U23 v Fulham U23 | W | 1-0 |
| England - Premier League 2 | 2019/08/30 18:00 | Man Utd U23 v West Ham U23 | D | 2-2 |
| England - Premier League 2 | 2019/08/23 18:00 | Newcastle U23 v Man Utd U23 | W | 0-4 |
| England - Premier League 2 | 2019/08/16 18:00 | Man Utd U23 v Reading U23 | W | 2-0 |