Head to Head
| England U23 Premier League Cup | 2018/02/23 19:01 | Middlesbrough U23 v Derby U23 | L | 2-1 |
| England U23 Premier League Cup | 2017/12/01 19:02 | Derby U23 v Middlesbrough U23 | W | 2-1 |
Home History
| England Premier League 2 | 2020/02/28 12:00 | Derby U23 v Brighton U23 | L | 1-4 |
| England U23 Premier League Cup | 2020/02/25 14:01 | Wolverhampton U23 v Derby U23 | W | 1-3 |
| England U23 Premier League Cup | 2020/02/21 14:00 | Birmingham U23 v Derby U23 | L | 1-0 |
| England Premier League 2 | 2020/02/17 19:00 | Everton U23 v Derby U23 | L | 2-1 |
| England U23 Premier League Cup | 2020/02/07 19:00 | Leeds U23 v Derby U23 | W | 1-2 |
| England Premier League 2 | 2020/02/03 12:00 | Blackburn U23 v Derby U23 | L | 2-0 |
| England Premier League 2 | 2020/01/13 19:00 | Derby U23 v Tottenham U23 | D | 2-2 |
| England Premier League 2 | 2020/01/03 19:00 | Arsenal U23 v Derby U23 | D | 2-2 |
Away History
| England Premier League 2 | 2020/02/28 19:00 | Middlesbrough U23 v Newcastle U23 | L | 0-2 |
| England U23 Premier League Cup | 2020/02/21 19:00 | Middlesbrough U23 v Crystal Palace U23 | D | 1-1 |
| 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 |