[8] Wolverhampton U23 1-1 Middlesbrough U23 [4] 2017-12-24 20:00
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 | 2017/12/11 19:00 | Southampton U23 v Wolverhampton U23 | W | 2-4 |
| England U23 Premier League Cup | 2017/12/05 19:02 | Wolverhampton U23 v Bournemouth U23 | W | 2-1 |
| England Premier League 2 | 2017/11/27 19:00 | Brighton U23 v Wolverhampton U23 | D | 1-1 |
| 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 |
Away History
| England Premier League 2 | 2017/12/10 12:00 | Norwich U23 v Middlesbrough U23 | L | 1-0 |
| England U23 Premier League Cup | 2017/12/01 19:02 | Derby U23 v Middlesbrough U23 | L | 2-1 |
| England Premier League 2 | 2017/11/26 13:00 | Middlesbrough U23 v Southampton U23 | D | 3-3 |
| 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 |
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