Head to Head
| Anglia - Premier League 2 | 2021/08/16 18:00 | Wolverhampton - U23 v Middlesbrough - U23 | L | 2-1 |
| Anglia - Premier League 2 | 2021/03/22 12:00 | Middlesbrough - U23 v Wolverhampton - U23 | D | 1-1 |
| Anglia - Premier League 2 | 2020/11/20 13:30 | Wolverhampton - U23 v Middlesbrough - U23 | W | 1-4 |
| Anglia - Premier League 2 | 2019/03/01 19:00 | Middlesbrough - U23 v Wolverhampton - U23 | D | 0-0 |
| Anglia - Premier League 2 | 2018/09/28 18:00 | Wolverhampton - U23 v Middlesbrough - U23 | L | 2-0 |
| Anglia - Premier League 2 | 2018/04/12 14:00 | Wolverhampton - U23 v Middlesbrough - U23 | D | 1-1 |
| Anglia - Premier League 2 | 2017/10/29 13:00 | Middlesbrough - U23 v Wolverhampton - U23 | W | 3-1 |
| Anglia - Premier League 2 | 2017/04/17 12:00 | Middlesbrough - U23 v Wolverhampton - U23 | L | 0-1 |
Home History
| Angol Premier League Cup - U23 | 2022/04/08 18:00 | Stoke - U23 v Middlesbrough - U23 | W | 1-2 |
| Anglia - Premier League 2 | 2022/04/01 18:00 | Middlesbrough - U23 v Newcastle - U23 | W | 4-2 |
| Anglia - Premier League 2 | 2022/03/18 19:00 | Middlesbrough - U23 v Fulham - U23 | D | 0-0 |
| Anglia - Premier League 2 | 2022/03/14 19:00 | Stoke - U23 v Middlesbrough - U23 | L | 1-0 |
| Anglia - Premier League 2 | 2022/02/27 13:00 | Birmingham - U23 v Middlesbrough - U23 | L | 4-2 |
| Angol Premier League Cup - U23 | 2022/02/11 18:00 | Nottm Forest - U23 v Middlesbrough - U23 | L | 2-1 |
| Anglia - Premier League 2 | 2022/02/04 15:00 | Norwich - U23 v Middlesbrough - U23 | L | 4-0 |
| Anglia - Premier League 2 | 2022/01/23 14:00 | Southampton - U23 v Middlesbrough - U23 | L | 1-0 |
Away History
| Angol Premier League Cup - U23 | 2022/04/10 13:00 | Peterborough - U23 v Wolverhampton - U23 | W | 0-1 |
| Anglia - Premier League 2 | 2022/04/01 18:00 | Nottm Forest - U23 v Wolverhampton - U23 | L | 1-0 |
| Anglia - Premier League 2 | 2022/03/25 12:00 | Southampton - U23 v Wolverhampton - U23 | W | 2-4 |
| Anglia - Premier League 2 | 2022/03/18 18:00 | Wolverhampton - U23 v Aston Villa - U23 | W | 3-0 |
| Anglia - Premier League 2 | 2022/03/14 18:00 | West Brom - U23 v Wolverhampton - U23 | W | 0-4 |
| Angol Premier League Cup - U23 | 2022/03/04 19:00 | Wigan - U23 v Wolverhampton - U23 | W | 0-1 |
| Anglia - Premier League 2 | 2022/02/28 19:00 | Wolverhampton - U23 v Reading - U23 | W | 4-3 |
| Angol Premier League Cup - U23 | 2022/02/22 14:00 | Wolverhampton - U23 v Exeter - U23 | L | 0-2 |