Head to Head
| England Premier League 2 | 2019/03/01 19:00 | Tottenham U23 v Chelsea U23 | D | 1-1 |
| England Premier League 2 | 2018/11/23 19:00 | Chelsea U23 v Tottenham U23 | D | 1-1 |
| 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 | 2019/08/23 18:00 | Man City U23 v Chelsea U23 | D | 2-2 |
| England Premier League 2 | 2019/08/19 18:00 | Chelsea U23 v Liverpool U23 | W | 3-0 |
| England Premier League 2 | 2019/08/12 18:00 | Derby U23 v Chelsea U23 | W | 0-1 |
| Club Friendly List | 2019/07/27 14:00 | Sutton Utd v Chelsea U23 | D | 2-2 |
| England Premier League 2 | 2019/05/03 18:00 | Brighton U23 v Chelsea U23 | W | 1-2 |
| England Premier League 2 | 2019/04/15 18:00 | Chelsea U23 v Arsenal U23 | L | 1-3 |
| England Premier League 2 | 2019/04/06 14:00 | Liverpool U23 v Chelsea U23 | L | 3-2 |
| England Premier League 2 | 2019/03/08 19:00 | Chelsea U23 v Man City U23 | W | 2-0 |
Away History
| England Premier League 2 | 2019/08/23 11:00 | Tottenham U23 v Derby U23 | L | 1-2 |
| England Premier League 2 | 2019/08/16 18:00 | Tottenham U23 v Man City U23 | W | 3-1 |
| England Premier League 2 | 2019/08/10 13:00 | Liverpool U23 v Tottenham U23 | W | 0-4 |
| Europe Friendlies | 2019/07/13 10:00 | Ebbsfleet United v Tottenham U23 | D | 2-2 |
| England Premier League 2 | 2019/04/29 18:00 | Tottenham U23 v Derby U23 | W | 3-1 |
| England Premier League 2 | 2019/04/15 18:00 | Swansea U23 v Tottenham U23 | W | 1-2 |
| England Premier League 2 | 2019/04/08 18:00 | Tottenham U23 v Blackburn U23 | L | 0-3 |
| England Premier League 2 | 2019/03/08 19:00 | Leicester U23 v Tottenham U23 | W | 1-2 |