[8] Middlesbrough U23 0-2 Man Utd U23 [6] 2018-09-23 12:00
Weather: Good Stadium: Riverside Pitch: Good Round: 1
Home History
| England Premier League 2 | 2018/09/17 18:00 | West Brom U23 v Middlesbrough U23 | W | 2-3 |
| England Premier League 2 | 2018/09/02 12:00 | Middlesbrough U23 v Aston Villa U23 | L | 1-2 |
| England Premier League 2 | 2018/08/27 18:00 | Stoke U23 v Middlesbrough U23 | D | 1-1 |
| England Premier League 2 | 2018/08/17 12:00 | Middlesbrough U23 v Fulham U23 | W | 4-3 |
| England Premier League 2 | 2018/08/10 18:00 | Southampton U23 v Middlesbrough U23 | L | 2-0 |
| England County Cup | 2018/05/16 18:31 | Middlesbrough U23 v Scarborough Athletic | W | 1-0 |
| England Premier League 2 | 2018/04/23 18:00 | Southampton U23 v Middlesbrough U23 | L | 2-1 |
| England Premier League 2 | 2018/04/15 12:00 | Middlesbrough U23 v West Brom U23 | W | 2-1 |
Away History
| England Premier League 2 | 2018/09/14 18:00 | Man Utd U23 v Reading U23 | D | 1-1 |
| England Premier League 2 | 2018/08/31 18:00 | Man Utd U23 v Stoke U23 | W | 1-0 |
| England Premier League 2 | 2018/08/24 18:00 | Southampton U23 v Man Utd U23 | D | 1-1 |
| England Premier League 2 | 2018/08/17 18:00 | Man Utd U23 v Aston Villa U23 | W | 3-1 |
| England Premier League 2 | 2018/08/10 18:00 | Fulham U23 v Man Utd U23 | D | 2-2 |
| England Premier League 2 | 2018/04/20 18:00 | Man Utd U23 v Everton U23 | D | 2-2 |
| England Premier League 2 | 2018/04/13 18:00 | Man City U23 v Man Utd U23 | D | 1-1 |
| England Premier League 2 | 2018/04/06 18:00 | Man Utd U23 v Sunderland U23 | W | 4-0 |