[9] Middlesbrough U23 0-0 Wolverhampton U23 [2] 2019-03-01 19:00
Weather: Cold Stadium: Riverside Pitch: Good Round: 1
Head to Head
| 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 |