[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 |
Home History
| England Premier League 2 | 2019/02/18 19:00 | Aston Villa U23 v Middlesbrough U23 | D | 1-1 |
| England Premier League 2 | 2019/01/13 13:00 | Middlesbrough U23 v Southampton U23 | L | 1-2 |
| England Premier League 2 | 2019/01/04 13:00 | Fulham U23 v Middlesbrough U23 | D | 2-2 |
| England Premier League 2 | 2018/12/14 19:00 | Middlesbrough U23 v West Brom U23 | D | 2-2 |
| England Premier League 2 | 2018/12/07 19:00 | Man Utd U23 v Middlesbrough U23 | L | 2-0 |
| England Premier League 2 | 2018/11/26 19:00 | Sunderland U23 v Middlesbrough U23 | W | 1-3 |
| England Premier League 2 | 2018/11/04 13:00 | Middlesbrough U23 v Norwich U23 | W | 2-1 |
| England Premier League 2 | 2018/10/26 18:00 | Newcastle U23 v Middlesbrough U23 | W | 1-3 |
Away History
| England U23 Premier League Cup | 2019/02/26 17:56 | Wolverhampton U23 v Swansea U23 | L | 0-2 |
| England U23 Premier League Cup | 2019/02/22 19:07 | Wolverhampton U23 v Oxford Utd U23 | W | 2-0 |
| England Premier League 2 | 2019/02/15 19:00 | Wolverhampton U23 v Norwich U23 | W | 4-0 |
| England Premier League 2 | 2019/01/25 14:00 | Wolverhampton U23 v Fulham U23 | W | 1-0 |
| England U23 Premier League Cup | 2019/01/21 19:01 | Hull U23 v Wolverhampton U23 | W | 0-1 |
| England Premier League 2 | 2019/01/11 19:00 | Wolverhampton U23 v Reading U23 | L | 1-2 |
| England Premier League 2 | 2019/01/07 19:00 | West Brom U23 v Wolverhampton U23 | W | 2-4 |
| England Premier League 2 | 2018/12/09 12:00 | Sunderland U23 v Wolverhampton U23 | W | 0-1 |