Head to Head
| England Premier League 2 | 2017/04/10 18:00 | West Ham U23 v Middlesbrough U23 | W | 1-3 |
| England Premier League 2 | 2016/10/21 18:00 | Middlesbrough U23 v West Ham U23 | L | 0-1 |
Home History
| England Premier League 2 | 2019/04/28 12:00 | Middlesbrough U23 v Newcastle U23 | L | 0-1 |
| England Premier League 2 | 2019/04/19 18:00 | Middlesbrough U23 v Stoke U23 | D | 2-2 |
| England Premier League 2 | 2019/04/12 18:00 | Norwich U23 v Middlesbrough U23 | W | 2-3 |
| England Premier League 2 | 2019/04/07 12:00 | Middlesbrough U23 v Sunderland U23 | D | 0-0 |
| England Premier League 2 | 2019/03/09 13:00 | Reading U23 v Middlesbrough U23 | D | 2-2 |
| England Premier League 2 | 2019/03/01 19:00 | Middlesbrough U23 v Wolverhampton U23 | D | 0-0 |
| 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 |
Away History
| England Premier League 2 | 2019/04/29 18:00 | West Ham U23 v Everton U23 | W | 2-1 |
| England Premier League 2 | 2019/04/15 18:00 | Derby U23 v West Ham U23 | D | 2-2 |
| England Premier League 2 | 2019/04/07 12:00 | West Ham U23 v Leicester U23 | W | 1-0 |
| England Premier League 2 | 2019/03/29 19:00 | Arsenal U23 v West Ham U23 | L | 1-0 |
| England Premier League 2 | 2019/03/11 19:00 | Swansea U23 v West Ham U23 | W | 0-3 |
| England Premier League 2 | 2019/03/04 19:00 | West Ham U23 v Blackburn U23 | L | 1-3 |
| England Premier League 2 | 2019/02/18 19:00 | West Ham U23 v Liverpool U23 | L | 0-1 |
| England Premier League 2 | 2019/01/13 12:00 | West Ham U23 v Tottenham U23 | D | 1-1 |