[8] Wolverhampton U23 1-1 Middlesbrough U23 [4] 2017-11-21 12:00
Weather: Foggy Pitch: Uneven and|cutting up Round: 19
Head to Head
| 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 | 2017/11/20 19:00 | Wolverhampton U23 v Norwich U23 | W | 4-2 |
| England U23 Premier League Cup | 2017/11/06 19:01 | Wolverhampton U23 v Norwich U23 | D | 3-3 |
| England Premier League 2 | 2017/10/29 13:00 | Middlesbrough U23 v Wolverhampton U23 | L | 3-1 |
| England Premier League 2 | 2017/10/23 18:00 | Wolverhampton U23 v Fulham U23 | L | 1-4 |
| England Premier League 2 | 2017/10/16 18:00 | Wolverhampton U23 v Aston Villa U23 | L | 0-2 |
| England U23 Premier League Cup | 2017/10/09 17:59 | Bury U23 v Wolverhampton U23 | W | 2-3 |
| England Premier League 2 | 2017/09/25 18:00 | Newcastle U23 v Wolverhampton U23 | W | 0-1 |
| England Premier League 2 | 2017/09/18 18:00 | Wolverhampton U23 v Reading U23 | L | 1-2 |
Away History
| England Premier League 2 | 2017/11/20 13:30 | West Brom U23 v Middlesbrough U23 | W | 0-1 |
| England U23 Premier League Cup | 2017/11/06 19:00 | Middlesbrough U23 v Birmingham U23 | L | 1-3 |
| England Premier League 2 | 2017/10/29 13:00 | Middlesbrough U23 v Wolverhampton U23 | W | 3-1 |
| England Premier League 2 | 2017/10/20 12:00 | Brighton U23 v Middlesbrough U23 | D | 2-2 |
| England Premier League 2 | 2017/10/15 12:00 | Middlesbrough U23 v Reading U23 | L | 3-4 |
| England U23 Premier League Cup | 2017/10/02 17:58 | Nottm Forest U23 v Middlesbrough U23 | W | 0-3 |
| England Premier League 2 | 2017/09/22 18:00 | Middlesbrough U23 v Stoke U23 | W | 2-1 |
| England Premier League 2 | 2017/09/15 18:00 | Middlesbrough U23 v Aston Villa U23 | W | 4-1 |