[5] West Ham U23 1-3 Middlesbrough U23 [10] 2017-02-19 18:00
Weather: Cold Stadium: Boleyn Ground Pitch: Excellent Round: 1
Head to Head
| England Premier League 2 | 2016/10/21 18:00 | Middlesbrough U23 v West Ham U23 | W | 0-1 |
Home History
| England U23 Premier League Cup | 2017/02/13 20:59 | West Ham U23 v Nottm Forest U23 | W | 3-0 |
| England U23 Premier League Cup | 2017/02/09 20:52 | West Ham U23 v Leicester U23 | D | 2-2 |
| England Premier League 2 | 2017/02/03 19:00 | Blackburn U23 v West Ham U23 | L | 2-1 |
| England Premier League 2 | 2017/01/27 19:00 | West Ham U23 v Aston Villa U23 | D | 0-0 |
| England Premier League 2 | 2017/01/16 19:00 | Brighton U23 v West Ham U23 | L | 3-0 |
| England Premier League 2 | 2017/01/09 19:00 | West Ham U23 v Norwich U23 | W | 2-1 |
| England Premier League 2 | 2016/12/19 19:00 | Wolverhampton U23 v West Ham U23 | W | 0-4 |
| England Premier League 2 | 2016/12/12 19:00 | West Ham U23 v Swansea U23 | L | 2-3 |
Away History
| 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 |
| England U23 Premier League Cup | 2017/01/23 17:01 | Middlesbrough U23 v Fulham U23 | L | 1-2 |
| England Premier League 2 | 2017/01/16 19:00 | Aston Villa U23 v Middlesbrough U23 | D | 0-0 |
| England Premier League 2 | 2016/12/19 19:00 | Swansea U23 v Middlesbrough U23 | L | 3-2 |
| England Premier League 2 | 2016/12/12 19:00 | Middlesbrough U23 v Norwich U23 | D | 2-2 |
| England U23 Premier League Cup | 2016/12/05 14:06 | AFC Wimbledon U23 v Middlesbrough U23 | W | 0-1 |
| England Premier League 2 | 2016/11/28 19:00 | West Brom U23 v Middlesbrough U23 | D | 0-0 |