[8] Middlesbrough U23 0-1 West Ham U23 [3] 2016-10-21 18:00
Weather: Cold Stadium: Riverside Pitch: Excellent Round: 1
Home History
| England Premier League 2 | 2016/10/14 18:00 | Stoke U23 v Middlesbrough U23 | L | 3-1 |
| England EFL Trophy | 2016/10/04 18:00 | Cambridge Utd v Middlesbrough U23 | L | 2-1 |
| England U23 Premier League Cup | 2016/09/30 15:01 | Fulham U23 v Middlesbrough U23 | L | 3-1 |
| England Premier League 2 | 2016/09/26 18:00 | Middlesbrough U23 v Aston Villa U23 | L | 1-2 |
| England Premier League 2 | 2016/09/19 18:00 | Wolverhampton U23 v Middlesbrough U23 | L | 2-1 |
| England Premier League 2 | 2016/09/12 18:00 | Middlesbrough U23 v Swansea U23 | W | 2-1 |
| England EFL Trophy | 2016/08/30 18:45 | Scunthorpe v Middlesbrough U23 | L | 2-1 |
| Club Friendly List | 2015/07/16 18:30 | Harrogate Railway v Middlesbrough U23 | W | 0-4 |
Away History
| England Premier League 2 | 2016/10/17 18:00 | Aston Villa U23 v West Ham U23 | L | 2-0 |
| England EFL Trophy | 2016/10/04 18:45 | Wycombe v West Ham U23 | L | 3-0 |
| England Premier League 2 | 2016/09/26 18:00 | West Ham U23 v Brighton U23 | D | 0-0 |
| England Premier League 2 | 2016/09/19 18:00 | Norwich U23 v West Ham U23 | W | 0-2 |
| England Premier League 2 | 2016/09/09 18:00 | West Ham U23 v Wolverhampton U23 | D | 2-2 |
| England EFL Trophy | 2016/08/30 18:45 | Coventry v West Ham U23 | L | 4-2 |
| Club Friendly List | 2016/07/30 13:00 | VVV v West Ham U23 | L | 6-1 |
| England U21 Premier League Cup | 2016/05/04 18:00 | Hull U21 v West Ham U23 | W | 4-5 |