[9] Middlesbrough U23 0-1 Wolverhampton U23 [2] 2017-04-17 12:00
Weather: Good Stadium: Riverside Pitch: Excellent Round: 1
Head to Head
| England Premier League 2 | 2016/09/19 18:00 | Wolverhampton U23 v Middlesbrough U23 | L | 2-1 |
Home History
| England Premier League 2 | 2017/04/10 18:00 | West Ham U23 v Middlesbrough U23 | W | 1-3 |
| England U23 Premier League Cup | 2017/03/20 13:00 | Reading U23 v Middlesbrough U23 | L | 4-1 |
| England Premier League 2 | 2017/03/13 19:00 | Middlesbrough U23 v Blackburn U23 | W | 4-1 |
| England Premier League 2 | 2017/03/03 19:00 | Brighton U23 v Middlesbrough U23 | L | 4-2 |
| England U23 Premier League Cup | 2017/02/27 14:56 | Middlesbrough U23 v AFC Wimbledon U23 | W | 1-0 |
| England Premier League 2 | 2017/02/20 19:00 | Middlesbrough U23 v West Brom U23 | W | 2-1 |
| England U23 Premier League Cup | 2017/02/13 15:04 | Charlton U23 v Middlesbrough U23 | L | 5-2 |
| England Premier League 2 | 2017/01/30 19:00 | Middlesbrough U23 v Stoke U23 | D | 2-2 |
Away History
| England Premier League 2 | 2017/04/10 18:00 | Wolverhampton U23 v Norwich U23 | W | 3-1 |
| England Premier League 2 | 2017/03/17 14:00 | Stoke U23 v Wolverhampton U23 | D | 1-1 |
| England Premier League 2 | 2017/03/13 19:00 | Swansea U23 v Wolverhampton U23 | D | 2-2 |
| England Premier League 2 | 2017/03/06 19:00 | Wolverhampton U23 v Aston Villa U23 | L | 1-2 |
| England U23 Premier League Cup | 2017/02/24 15:54 | Norwich U23 v Wolverhampton U23 | L | 5-0 |
| England Premier League 2 | 2017/02/20 19:00 | Wolverhampton U23 v Brighton U23 | W | 2-1 |
| England Premier League 2 | 2017/02/15 19:00 | Wolverhampton U23 v Stoke U23 | D | 1-1 |
| England U23 Premier League Cup | 2017/02/07 20:51 | Wolverhampton U23 v Portsmouth U23 | L | 2-4 |