Head to Head
| 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 | L | 3-1 |
| England Premier League 2 | 2017/04/17 12:00 | Middlesbrough U23 v Wolverhampton U23 | W | 0-1 |
| England Premier League 2 | 2016/09/19 18:00 | Wolverhampton U23 v Middlesbrough U23 | W | 2-1 |
Home History
| England Premier League 2 | 2018/09/24 18:00 | Wolverhampton U23 v Sunderland U23 | W | 7-0 |
| England Premier League 2 | 2018/09/14 18:00 | Fulham U23 v Wolverhampton U23 | L | 1-0 |
| England Premier League 2 | 2018/08/31 18:00 | Norwich U23 v Wolverhampton U23 | W | 1-3 |
| England Premier League 2 | 2018/08/27 18:00 | Wolverhampton U23 v Newcastle U23 | W | 2-0 |
| England Premier League 2 | 2018/08/17 18:00 | Wolverhampton U23 v West Brom U23 | W | 4-1 |
| England Premier League 2 | 2018/04/23 18:00 | Wolverhampton U23 v Brighton U23 | L | 0-5 |
| England Premier League 2 | 2018/04/15 13:00 | Norwich U23 v Wolverhampton U23 | L | 2-1 |
| England Premier League 2 | 2018/04/12 14:00 | Wolverhampton U23 v Middlesbrough U23 | D | 1-1 |
Away History
| England Premier League 2 | 2018/09/23 12:00 | Middlesbrough U23 v Man Utd U23 | L | 0-2 |
| England Premier League 2 | 2018/09/17 18:00 | West Brom U23 v Middlesbrough U23 | W | 2-3 |
| England Premier League 2 | 2018/09/02 12:00 | Middlesbrough U23 v Aston Villa U23 | L | 1-2 |
| England Premier League 2 | 2018/08/27 18:00 | Stoke U23 v Middlesbrough U23 | D | 1-1 |
| England Premier League 2 | 2018/08/17 12:00 | Middlesbrough U23 v Fulham U23 | W | 4-3 |
| England Premier League 2 | 2018/08/10 18:00 | Southampton U23 v Middlesbrough U23 | L | 2-0 |
| England County Cup | 2018/05/16 18:31 | Middlesbrough U23 v Scarborough Athletic | W | 1-0 |
| England Premier League 2 | 2018/04/23 18:00 | Southampton U23 v Middlesbrough U23 | L | 2-1 |