Head to Head
| England U23 Premier League Cup | 2019/12/02 14:00 | Crystal Palace U23 v Middlesbrough U23 | W | 1-5 |
Home History
| England Premier League 2 | 2020/02/17 19:00 | Reading U23 v Middlesbrough U23 | W | 0-1 |
| England U23 Premier League Cup | 2020/02/07 19:00 | Middlesbrough U23 v Blackburn U23 | W | 4-1 |
| England Premier League 2 | 2020/02/02 13:00 | Middlesbrough U23 v Fulham U23 | W | 1-0 |
| England U23 Premier League Cup | 2020/01/20 13:00 | Burnley U23 v Middlesbrough U23 | W | 1-2 |
| England Premier League 2 | 2020/01/13 13:00 | Swansea U23 v Middlesbrough U23 | L | 5-1 |
| England Premier League 2 | 2020/01/06 19:00 | Middlesbrough U23 v Norwich U23 | L | 3-4 |
| England Premier League 2 | 2019/12/16 19:00 | Stoke U23 v Middlesbrough U23 | W | 2-3 |
| England Premier League 2 | 2019/12/09 19:00 | Aston Villa U23 v Middlesbrough U23 | L | 5-3 |
Away History
| England U23 Development League | 2020/02/18 13:30 | Millwall U23 v Crystal Palace U23 | L | 1-0 |
| England U23 Development League | 2020/02/10 13:00 | Crystal Palace U23 v Coventry U23 | D | 0-0 |
| England U23 Premier League Cup | 2020/02/06 14:00 | Crystal Palace U23 v Burnley U23 | L | 0-1 |
| England U23 Development League | 2020/02/03 13:00 | Bristol City U23 v Crystal Palace U23 | L | 1-0 |
| England U23 Development League | 2020/01/29 13:00 | Crystal Palace U23 v Cardiff U23 | L | 2-3 |
| England U23 Premier League Cup | 2020/01/25 13:03 | Blackburn U23 v Crystal Palace U23 | L | 2-0 |
| England U23 Development League | 2020/01/22 13:00 | Charlton U23 v Crystal Palace U23 | L | 2-1 |
| England U23 Development League | 2020/01/06 13:00 | Crystal Palace U23 v QPR U23 | D | 3-3 |