Head to Head
| Anglia - Premier League 2 | 2021/04/23 14:00 | Middlesbrough - U23 v Aston Villa - U23 | W | 4-1 |
| Anglia - Premier League 2 | 2020/12/18 14:00 | Aston Villa - U23 v Middlesbrough - U23 | D | 1-1 |
| Anglia - Premier League 2 | 2019/12/09 19:00 | Aston Villa - U23 v Middlesbrough - U23 | L | 5-3 |
| Anglia - Premier League 2 | 2019/08/09 18:00 | Middlesbrough - U23 v Aston Villa - U23 | W | 1-0 |
| Anglia - Premier League 2 | 2019/02/18 19:00 | Aston Villa - U23 v Middlesbrough - U23 | D | 1-1 |
| Anglia - Premier League 2 | 2018/09/02 12:00 | Middlesbrough - U23 v Aston Villa - U23 | L | 1-2 |
| Angol Premier League Cup - U23 | 2018/04/09 18:00 | Middlesbrough - U23 v Aston Villa - U23 | L | 1-2 |
| Anglia - Premier League 2 | 2018/01/29 13:00 | Aston Villa - U23 v Middlesbrough - U23 | L | 4-0 |
Home History
| Anglia - Premier League 2 | 2021/08/16 18:00 | Wolverhampton - U23 v Middlesbrough - U23 | L | 2-1 |
| Anglia - Premier League 2 | 2021/05/07 12:00 | Middlesbrough - U23 v Crystal Palace - U23 | L | 0-1 |
| Anglia - Premier League 2 | 2021/05/03 12:00 | Crystal Palace - U23 v Middlesbrough - U23 | L | 3-2 |
| Anglia - Premier League 2 | 2021/04/23 14:00 | Middlesbrough - U23 v Aston Villa - U23 | W | 4-1 |
| Anglia - Premier League 2 | 2021/04/16 13:00 | Middlesbrough - U23 v Fulham - U23 | W | 1-0 |
| Anglia - Premier League 2 | 2021/04/09 12:00 | Reading - U23 v Middlesbrough - U23 | W | 2-4 |
| Anglia - Premier League 2 | 2021/03/22 12:00 | Middlesbrough - U23 v Wolverhampton - U23 | D | 1-1 |
| Anglia - Premier League 2 | 2021/03/12 13:00 | West Brom - U23 v Middlesbrough - U23 | W | 0-1 |
Away History
| Anglia - Premier League 2 | 2021/08/13 18:00 | Aston Villa - U23 v Nottm Forest - U23 | W | 5-2 |
| Anglia - Premier League 2 | 2021/05/07 18:00 | Newcastle - U23 v Aston Villa - U23 | W | 1-2 |
| Anglia - Premier League 2 | 2021/05/02 13:00 | Aston Villa - U23 v Newcastle - U23 | D | 1-1 |
| Anglia - Premier League 2 | 2021/04/23 14:00 | Middlesbrough - U23 v Aston Villa - U23 | L | 4-1 |
| Anglia - Premier League 2 | 2021/04/16 18:00 | Aston Villa - U23 v Leeds - U23 | L | 1-2 |
| Anglia - Premier League 2 | 2021/04/09 12:00 | Fulham - U23 v Aston Villa - U23 | L | 4-1 |
| Anglia - Premier League 2 | 2021/04/02 14:00 | Aston Villa - U23 v Wolverhampton - U23 | W | 4-0 |
| Anglia - Premier League 2 | 2021/03/19 19:00 | Aston Villa - U23 v Stoke - U23 | L | 3-4 |