Home History
| England Premier League 2 | 2019/10/18 18:00 | Middlesbrough U23 v Reading U23 | W | 2-1 |
| England U23 Premier League Cup | 2019/10/06 11:59 | Middlesbrough U23 v Burnley U23 | D | 1-1 |
| England Premier League 2 | 2019/09/27 11:00 | Fulham U23 v Middlesbrough U23 | W | 2-4 |
| England Premier League 2 | 2019/09/20 18:00 | Middlesbrough U23 v West Ham U23 | L | 3-4 |
| England Premier League 2 | 2019/09/16 18:00 | Sunderland U23 v Middlesbrough U23 | W | 2-3 |
| England Premier League 2 | 2019/08/30 18:00 | Norwich U23 v Middlesbrough U23 | D | 2-2 |
| England Premier League 2 | 2019/08/23 12:00 | Middlesbrough U23 v Swansea U23 | W | 3-2 |
| England Premier League 2 | 2019/08/16 18:00 | Middlesbrough U23 v Stoke U23 | L | 0-2 |
Away History
| England U23 Development League | 2019/10/21 12:00 | Crystal Palace U23 v Charlton U23 | L | 1-2 |
| England U23 Premier League Cup | 2019/10/17 12:11 | Crystal Palace U23 v Blackburn U23 | L | 1-3 |
| England U23 Development League | 2019/10/14 12:00 | Crystal Palace U23 v Watford U23 | L | 0-2 |
| England U23 Development League | 2019/09/23 12:00 | QPR U23 v Crystal Palace U23 | L | 3-1 |
| England U23 Development League | 2019/09/16 18:00 | Bolton U23 v Crystal Palace U23 | W | 1-5 |
| England U23 Development League | 2019/09/09 12:00 | Crystal Palace U23 v Leeds U23 | D | 0-0 |
| England U23 Development League | 2019/09/02 12:00 | Barnsley U23 v Crystal Palace U23 | L | 3-0 |
| England U23 Development League | 2019/08/27 12:00 | Crystal Palace U23 v Hull U23 | L | 1-3 |