Home History
| England Premier League 2 | 2021/05/07 15:00 | Blackburn U23 v Chelsea U23 | W | 2-4 |
| England Premier League 2 | 2021/04/30 18:00 | Chelsea U23 v Blackburn U23 | W | 1-0 |
| England Premier League 2 | 2021/04/23 18:00 | Man Utd U23 v Chelsea U23 | L | 4-2 |
| England Premier League 2 | 2021/04/18 12:00 | Tottenham U23 v Chelsea U23 | W | 1-4 |
| England Premier League 2 | 2021/04/12 18:00 | Chelsea U23 v Southampton U23 | W | 3-1 |
| England Premier League 2 | 2021/04/06 18:00 | West Ham U23 v Chelsea U23 | D | 1-1 |
| England Premier League 2 | 2021/03/21 10:30 | Chelsea U23 v Man City U23 | D | 2-2 |
| England Premier League 2 | 2021/03/12 19:00 | Chelsea U23 v Everton U23 | W | 2-1 |
Away History
| Club Friendly List | 2021/07/24 14:00 | Luton v Portsmouth | D | 1-1 |
| Club Friendly List | 2021/07/20 13:00 | Bristol City v Portsmouth | D | 3-3 |
| Club Friendly List | 2021/07/10 14:00 | Havant and W v Portsmouth | W | 2-5 |
| England League 1 | 2021/05/09 11:00 | Portsmouth v Accrington Stanley | L | 0-1 |
| England League 1 | 2021/05/01 14:00 | AFC Wimbledon v Portsmouth | W | 1-3 |
| England League 1 | 2021/04/27 18:00 | Accrington Stanley v Portsmouth | D | 3-3 |
| England League 1 | 2021/04/24 12:00 | Portsmouth v Bristol Rovers | W | 1-0 |
| England League 1 | 2021/04/20 17:00 | Swindon v Portsmouth | L | 3-1 |