[5] Chelsea U21 2-0 Southampton U21 [16] 2024-01-18 14:00
Stadium: The Electrical Services Stadium Round: 20
Home History
| England Premier League 2 | 2024/01/12 19:00 | Chelsea U21 v Man Utd U21 | W | 3-2 |
| Premier League International Cup | 2024/01/09 19:00 | Chelsea U21 v Valencia U21 | D | 1-1 |
| Premier League International Cup | 2023/12/20 19:00 | Chelsea U21 v Celtic U21 | W | 3-1 |
| England Premier League 2 | 2023/12/17 13:00 | Liverpool U21 v Chelsea U21 | L | 2-1 |
| England U21 Premier League Cup | 2023/12/12 19:00 | Luton U21 v Chelsea U21 | W | 1-2 |
| Europe Friendlies | 2023/11/28 18:00 | Chelsea U21 v Strasbourg II | L | 1-4 |
| England U21 Premier League Cup | 2023/11/12 13:00 | Leeds U21 v Chelsea U21 | W | 1-2 |
| England EFL Trophy | 2023/11/07 19:00 | Oxford Utd v Chelsea U21 | L | 5-0 |
Away History
| England Premier League 2 | 2024/01/12 19:00 | Southampton U21 v Tottenham U21 | L | 2-3 |
| Premier League International Cup | 2023/12/20 19:00 | Southampton U21 v Dinamo Zagreb U21 | D | 2-2 |
| England Premier League 2 | 2023/12/15 11:30 | Southampton U21 v Derby U21 | W | 2-1 |
| England Premier League 2 | 2023/12/04 19:00 | Everton U21 v Southampton U21 | L | 5-0 |
| Premier League International Cup | 2023/11/28 19:00 | Southampton U21 v Valencia U21 | L | 0-2 |
| England Premier League 2 | 2023/11/03 12:00 | Southampton U21 v Sunderland U21 | L | 1-2 |
| England Premier League 2 | 2023/10/30 19:00 | Wolverhampton U21 v Southampton U21 | L | 2-1 |
| Premier League International Cup | 2023/10/04 18:00 | Southampton U21 v Lyon U21 | L | 3-4 |