[6] Tottenham U23 0-1 Chelsea U23 [3] 2020-01-06 19:00
Stadium: White Hart Lane Pitch: Regular Round: 14
Head to Head
| 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 |
| 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 | L | 3-1 |
Home History
| England Premier League 2 | 2019/12/15 12:00 | Man City U23 v Tottenham U23 | L | 2-0 |
| England Premier League 2 | 2019/12/06 12:00 | Tottenham U23 v Liverpool U23 | W | 4-0 |
| England Premier League 2 | 2019/11/22 19:00 | Everton U23 v Tottenham U23 | W | 1-3 |
| England Premier League 2 | 2019/11/01 19:00 | Tottenham U23 v Arsenal U23 | L | 1-3 |
| England Premier League 2 | 2019/10/26 12:00 | Wolverhampton U23 v Tottenham U23 | W | 1-2 |
| England Premier League 2 | 2019/10/18 18:00 | Tottenham U23 v Leicester U23 | L | 0-2 |
| England Premier League 2 | 2019/09/27 18:00 | Brighton U23 v Tottenham U23 | L | 4-1 |
| England Premier League 2 | 2019/09/23 18:00 | Blackburn U23 v Tottenham U23 | L | 4-0 |
Away History
| England Premier League 2 | 2019/12/14 15:00 | Liverpool U23 v Chelsea U23 | D | 1-1 |
| England Premier League 2 | 2019/12/07 12:00 | Chelsea U23 v Derby U23 | D | 3-3 |
| England Premier League 2 | 2019/11/23 12:45 | Wolverhampton U23 v Chelsea U23 | D | 1-1 |
| England Premier League 2 | 2019/11/02 12:00 | Chelsea U23 v Blackburn U23 | W | 2-1 |
| England Premier League 2 | 2019/10/18 18:00 | Chelsea U23 v Arsenal U23 | W | 3-1 |
| England Premier League 2 | 2019/09/28 11:00 | Leicester U23 v Chelsea U23 | D | 2-2 |
| England Premier League 2 | 2019/09/21 14:00 | Southampton U23 v Chelsea U23 | W | 0-2 |
| England Premier League 2 | 2019/09/13 18:00 | Chelsea U23 v Brighton U23 | W | 2-1 |