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 | 2022/02/04 19:00 | Arsenal U23 v Chelsea U23 | L | 3-1 |
| England Premier League 2 | 2022/01/24 19:00 | Chelsea U23 v Man City U23 | L | 0-1 |
| England Premier League 2 | 2022/01/17 13:00 | Crystal Palace U23 v Chelsea U23 | L | 3-2 |
| England Premier League 2 | 2022/01/08 12:30 | Chelsea U23 v Leicester U23 | W | 5-0 |
| England Premier League 2 | 2021/12/03 19:00 | Derby U23 v Chelsea U23 | L | 3-1 |
| 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 |
Away History
| England Premier League 2 | 2022/02/07 12:00 | Tottenham U23 v Crystal Palace U23 | L | 1-4 |
| England Premier League 2 | 2022/01/24 19:00 | Everton U23 v Tottenham U23 | L | 1-0 |
| England Premier League 2 | 2022/01/17 19:00 | Tottenham U23 v Blackburn U23 | D | 1-1 |
| England Premier League 2 | 2022/01/10 19:00 | Man Utd U23 v Tottenham U23 | D | 1-1 |
| England Premier League 2 | 2021/12/04 12:00 | Tottenham U23 v Man City U23 | W | 3-0 |
| 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 |