Head to Head
| England Premier League 2 | 2021/08/16 18:00 | Tottenham U23 v Chelsea U23 | D | 2-2 |
| England Premier League 2 | 2021/04/18 12:00 | Tottenham U23 v Chelsea U23 | W | 1-4 |
| England Premier League 2 | 2020/12/14 19:00 | Chelsea U23 v Tottenham U23 | W | 3-2 |
| England Premier League 2 | 2020/01/06 19:00 | Tottenham U23 v Chelsea U23 | W | 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 | L | 1-2 |
Home History
| England Premier League 2 | 2021/11/26 19:00 | Chelsea U23 v Brighton U23 | D | 1-1 |
| England Premier League 2 | 2021/11/19 13:00 | Leeds U23 v Chelsea U23 | W | 1-3 |
| England Premier League 2 | 2021/11/06 11:30 | Chelsea U23 v Crystal Palace U23 | L | 1-2 |
| England Premier League 2 | 2021/10/30 12:00 | Chelsea U23 v Everton U23 | D | 1-1 |
| England Premier League 2 | 2021/10/23 16:00 | Leicester U23 v Chelsea U23 | D | 1-1 |
| England Premier League 2 | 2021/10/16 12:00 | Chelsea U23 v Derby U23 | W | 2-0 |
| England Premier League 2 | 2021/10/03 11:00 | Chelsea U23 v Blackburn U23 | L | 0-1 |
| England Premier League 2 | 2021/09/24 18:00 | Chelsea U23 v Liverpool U23 | W | 4-3 |
Away History
| England Premier League 2 | 2021/11/26 19:00 | Tottenham U23 v Everton U23 | W | 4-0 |
| England Premier League 2 | 2021/11/22 19:00 | Leicester U23 v Tottenham U23 | W | 1-4 |
| England Premier League 2 | 2021/11/05 19:00 | Brighton U23 v Tottenham U23 | D | 1-1 |
| England Premier League 2 | 2021/10/30 11:00 | Tottenham U23 v Man Utd U23 | W | 1-0 |
| England Premier League 2 | 2021/10/23 14:00 | Man City U23 v Tottenham U23 | W | 1-3 |
| England Premier League 2 | 2021/10/18 18:00 | Tottenham U23 v West Ham U23 | L | 3-4 |
| England Premier League 2 | 2021/10/01 12:00 | Crystal Palace U23 v Tottenham U23 | L | 4-3 |
| England Premier League 2 | 2021/09/27 18:00 | Tottenham U23 v Derby U23 | W | 3-1 |