Away History
| Anglia - Premier League 2 | 2016/11/28 19:00 | West Brom U23 v Middlesbrough U23 | D | 0-0 |
| Anglia - Premier League 2 | 2016/11/18 13:00 | Middlesbrough U23 v Fulham U23 | L | 1-4 |
| Anglia - Premier League Cup U23 | 2016/11/11 20:05 | Middlesbrough U23 v Charlton U23 | W | 1-0 |
| Anglia - EFL Trophy | 2016/11/08 19:45 | Middlesbrough U23 v Shrewsbury | L | 0-3 |
| Anglia - Premier League 2 | 2016/10/31 19:00 | Newcastle U23 v Middlesbrough U23 | L | 2-0 |
| Anglia - Premier League 2 | 2016/10/21 18:00 | Middlesbrough U23 v West Ham U23 | L | 0-1 |
| Anglia - Premier League 2 | 2016/10/14 18:00 | Stoke U23 v Middlesbrough U23 | L | 3-1 |
| Anglia - EFL Trophy | 2016/10/04 18:00 | Cambridge Utd v Middlesbrough U23 | L | 2-1 |