Head to Head
| England Premier League 2 | 2021/08/16 18:00 | Wolverhampton U23 v Middlesbrough U23 | L | 2-1 |
| England Premier League 2 | 2021/03/22 12:00 | Middlesbrough U23 v Wolverhampton U23 | D | 1-1 |
| 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 |
Home History
| England Premier League 2 | 2022/01/23 14:00 | Southampton U23 v Middlesbrough U23 | L | 1-0 |
| England Premier League 2 | 2022/01/16 12:00 | Middlesbrough U23 v Sunderland U23 | W | 3-2 |
| England Premier League 2 | 2022/01/10 14:30 | Aston Villa U23 v Middlesbrough U23 | W | 1-2 |
| England U23 Premier League Cup | 2022/01/05 13:00 | QPR U23 v Middlesbrough U23 | W | 0-5 |
| England U23 Premier League Cup | 2022/01/02 13:00 | Middlesbrough U23 v Blackburn U23 | L | 2-4 |
| England Premier League 2 | 2021/12/06 18:00 | West Brom U23 v Middlesbrough U23 | L | 3-2 |
| England Premier League 2 | 2021/11/29 19:00 | Reading U23 v Middlesbrough U23 | L | 2-1 |
| England Premier League 2 | 2021/11/21 13:00 | Middlesbrough U23 v Norwich U23 | W | 3-2 |
Away History
| England Premier League 2 | 2022/01/24 19:00 | Sunderland U23 v Wolverhampton U23 | W | 1-2 |
| England Premier League 2 | 2022/01/17 19:00 | Wolverhampton U23 v Burnley U23 | D | 1-1 |
| England U23 Premier League Cup | 2021/12/13 14:00 | West Ham U23 v Wolverhampton U23 | D | 0-0 |
| England Premier League 2 | 2021/12/03 19:00 | Fulham U23 v Wolverhampton U23 | L | 4-2 |
| England Premier League 2 | 2021/11/29 19:00 | Wolverhampton U23 v Norwich U23 | L | 0-5 |
| England U23 Premier League Cup | 2021/11/25 14:00 | Swansea U23 v Wolverhampton U23 | W | 0-2 |
| England Premier League 2 | 2021/11/19 19:00 | Birmingham U23 v Wolverhampton U23 | W | 1-2 |
| England Premier League 2 | 2021/11/05 19:00 | Wolverhampton U23 v West Brom U23 | D | 1-1 |