Head to Head
| England Premier League 2 | 2020/11/20 13:30 | Wolverhampton U23 v Middlesbrough U23 | W | 1-4 |
| England Premier League 2 | 2019/03/01 19:00 | Middlesbrough U23 v Wolverhampton U23 | D | 0-0 |
| England Premier League 2 | 2018/09/28 18:00 | Wolverhampton U23 v Middlesbrough U23 | L | 2-0 |
| England Premier League 2 | 2018/04/12 14:00 | Wolverhampton U23 v Middlesbrough U23 | D | 1-1 |
| England Premier League 2 | 2017/10/29 13:00 | Middlesbrough U23 v Wolverhampton U23 | W | 3-1 |
| England Premier League 2 | 2017/04/17 12:00 | Middlesbrough U23 v Wolverhampton U23 | L | 0-1 |
| England Premier League 2 | 2016/09/19 18:00 | Wolverhampton U23 v Middlesbrough U23 | L | 2-1 |
Home History
| England Premier League 2 | 2021/03/12 13:00 | West Brom U23 v Middlesbrough U23 | W | 0-1 |
| England Premier League 2 | 2021/03/05 14:00 | Middlesbrough U23 v Newcastle U23 | W | 2-1 |
| England Premier League 2 | 2021/02/26 14:00 | Middlesbrough U23 v Norwich U23 | L | 0-3 |
| England Premier League 2 | 2021/02/22 14:00 | Burnley U23 v Middlesbrough U23 | L | 3-2 |
| England Premier League 2 | 2021/02/15 13:30 | Middlesbrough U23 v Sunderland U23 | D | 1-1 |
| England Premier League 2 | 2021/02/07 13:00 | Middlesbrough U23 v Leeds U23 | L | 2-4 |
| England Premier League 2 | 2021/01/25 15:00 | Stoke U23 v Middlesbrough U23 | L | 2-0 |
| England Premier League 2 | 2020/12/18 14:00 | Aston Villa U23 v Middlesbrough U23 | D | 1-1 |
Away History
| England Premier League 2 | 2021/03/15 13:00 | Wolverhampton U23 v Sunderland U23 | D | 0-0 |
| England Premier League 2 | 2021/03/05 13:00 | Wolverhampton U23 v Leeds U23 | L | 0-2 |
| England Premier League 2 | 2021/02/26 12:00 | Fulham U23 v Wolverhampton U23 | W | 0-2 |
| England Premier League 2 | 2021/02/22 14:00 | Wolverhampton U23 v Crystal Palace U23 | W | 2-0 |
| England Premier League 2 | 2021/01/31 12:00 | Stoke U23 v Wolverhampton U23 | L | 3-1 |
| England Premier League 2 | 2021/01/18 13:30 | Burnley U23 v Wolverhampton U23 | D | 0-0 |
| England Premier League 2 | 2020/12/21 13:00 | Norwich U23 v Wolverhampton U23 | W | 1-2 |
| England Premier League 2 | 2020/12/14 12:00 | West Brom U23 v Wolverhampton U23 | W | 2-4 |