Head to Head
| England Premier League 2 | 2018/04/13 18:05 | Chelsea U23 v Tottenham U23 | L | 1-2 |
| England Premier League 2 | 2017/11/18 12:00 | Tottenham U23 v Chelsea U23 | W | 2-3 |
| England Premier League 2 | 2017/01/06 13:05 | Tottenham U23 v Chelsea U23 | D | 2-2 |
| England Premier League 2 | 2016/09/09 18:05 | Chelsea U23 v Tottenham U23 | W | 3-1 |
Home History
| England Premier League 2 | 2018/11/03 13:00 | Arsenal U23 v Chelsea U23 | W | 4-5 |
| England Premier League 2 | 2018/10/27 11:00 | Chelsea U23 v Brighton U23 | L | 2-3 |
| England Premier League 2 | 2018/10/20 11:00 | Man City U23 v Chelsea U23 | W | 1-4 |
| England Premier League 2 | 2018/09/29 11:00 | Chelsea U23 v Liverpool U23 | L | 1-3 |
| England Premier League 2 | 2018/09/22 12:00 | West Ham U23 v Chelsea U23 | W | 1-2 |
| England Premier League 2 | 2018/09/16 11:00 | Chelsea U23 v Leicester U23 | D | 1-1 |
| England Premier League 2 | 2018/09/02 13:00 | Swansea U23 v Chelsea U23 | W | 0-1 |
| England Premier League 2 | 2018/08/24 18:00 | Chelsea U23 v Derby U23 | L | 0-1 |
Away History
| England Premier League 2 | 2018/11/02 12:00 | Tottenham U23 v Swansea U23 | L | 1-4 |
| England Premier League 2 | 2018/10/28 14:00 | Derby U23 v Tottenham U23 | L | 1-0 |
| England Premier League 2 | 2018/10/19 11:00 | Tottenham U23 v Leicester U23 | W | 1-0 |
| England Premier League 2 | 2018/09/28 18:00 | Blackburn U23 v Tottenham U23 | W | 1-3 |
| England Premier League 2 | 2018/09/23 12:00 | Everton U23 v Tottenham U23 | L | 6-0 |
| England Premier League 2 | 2018/09/14 18:00 | Tottenham U23 v Man City U23 | W | 2-0 |
| England Premier League 2 | 2018/08/31 18:00 | Arsenal U23 v Tottenham U23 | L | 2-1 |
| England Premier League 2 | 2018/08/24 18:00 | Tottenham U23 v Brighton U23 | D | 1-1 |