Head to Head
| England Premier League 2 | 2021/04/18 12:00 | Tottenham U23 v Chelsea U23 | L | 1-4 |
| England Premier League 2 | 2020/12/14 19:00 | Chelsea U23 v Tottenham U23 | L | 3-2 |
| England Premier League 2 | 2020/01/06 19:00 | Tottenham U23 v Chelsea U23 | L | 0-1 |
| England Premier League 2 | 2019/08/30 18:00 | Chelsea U23 v Tottenham U23 | D | 2-2 |
| 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 | W | 1-2 |
| England Premier League 2 | 2017/11/18 12:00 | Tottenham U23 v Chelsea U23 | L | 2-3 |
Home History
| England Premier League 2 | 2021/05/07 16:00 | Tottenham U23 v Man City U23 | L | 1-6 |
| England Premier League 2 | 2021/04/30 18:00 | Man City U23 v Tottenham U23 | L | 4-1 |
| England Premier League 2 | 2021/04/23 11:00 | Tottenham U23 v Liverpool U23 | W | 4-1 |
| England Premier League 2 | 2021/04/18 12:00 | Tottenham U23 v Chelsea U23 | L | 1-4 |
| England Premier League 2 | 2021/04/12 18:00 | Leicester U23 v Tottenham U23 | W | 1-3 |
| England Premier League 2 | 2021/03/19 12:00 | Tottenham U23 v Man Utd U23 | W | 3-0 |
| England Premier League 2 | 2021/03/15 19:00 | Derby U23 v Tottenham U23 | L | 1-0 |
| England Premier League 2 | 2021/03/05 12:00 | Tottenham U23 v Everton U23 | W | 2-1 |
Away History
| UK Friendlies | 2021/07/27 17:00 | Chelsea U23 v Portsmouth | W | 2-0 |
| England Premier League 2 | 2021/05/07 15:00 | Blackburn U23 v Chelsea U23 | W | 2-4 |
| England Premier League 2 | 2021/04/30 18:00 | Chelsea U23 v Blackburn U23 | W | 1-0 |
| England Premier League 2 | 2021/04/23 18:00 | Man Utd U23 v Chelsea U23 | L | 4-2 |
| England Premier League 2 | 2021/04/18 12:00 | Tottenham U23 v Chelsea U23 | W | 1-4 |
| England Premier League 2 | 2021/04/12 18:00 | Chelsea U23 v Southampton U23 | W | 3-1 |
| England Premier League 2 | 2021/04/06 18:00 | West Ham U23 v Chelsea U23 | D | 1-1 |
| England Premier League 2 | 2021/03/21 10:30 | Chelsea U23 v Man City U23 | D | 2-2 |