Home History
| England EFL Trophy | 2025/10/28 19:00 | Walsall v Chelsea U21 | D | 0-0 |
| England Premier League 2 | 2025/10/25 13:00 | Chelsea U21 v Arsenal U21 | W | 2-1 |
| Premier League International Cup | 2025/10/18 13:00 | Chelsea U21 v Dinamo Zagreb U21 | L | 1-2 |
| England Premier League 2 | 2025/10/05 11:00 | Burnley U21 v Chelsea U21 | W | 0-1 |
| England Premier League 2 | 2025/09/27 10:00 | Chelsea U21 v Stoke U21 | L | 1-2 |
| England EFL Trophy | 2025/09/23 18:00 | Northampton v Chelsea U21 | L | 3-0 |
| England Premier League 2 | 2025/09/20 13:00 | Chelsea U21 v Ipswich U21 | L | 2-4 |
| England Premier League 2 | 2025/08/29 18:00 | Aston Villa U21 v Chelsea U21 | W | 1-2 |
Away History
| Premier League International Cup | 2025/01/22 19:00 | Sunderland U21 v Benfica U21 | L | 2-1 |
| Premier League International Cup | 2024/12/18 19:00 | Middlesbrough U21 v Benfica U21 | W | 0-1 |
| Premier League International Cup | 2024/10/17 18:00 | Blackburn U21 v Benfica U21 | D | 1-1 |
| Premier League International Cup | 2024/09/24 18:00 | West Ham U21 v Benfica U21 | D | 2-2 |
| Premier League International Cup | 2024/01/24 19:00 | Everton U21 v Benfica U21 | L | 2-1 |
| Premier League International Cup | 2024/01/08 19:00 | Fulham U21 v Benfica U21 | L | 3-1 |
| Premier League International Cup | 2023/12/06 19:00 | Crystal Palace U21 v Benfica U21 | L | 2-1 |
| Premier League International Cup | 2023/10/22 13:00 | Liverpool U21 v Benfica U21 | D | 1-1 |