Home History
| England League 2 | 2022/10/15 14:00 | Leyton Orient v Northampton | D | 0-0 |
| England League 2 | 2022/10/08 14:00 | Doncaster v Leyton Orient | D | 1-1 |
| England League 2 | 2022/10/01 14:00 | Leyton Orient v Newport County | L | 1-2 |
| England League 2 | 2022/09/24 14:00 | Barrow v Leyton Orient | W | 0-2 |
| England EFL Trophy | 2022/09/20 18:00 | Leyton Orient v Sutton Utd | W | 3-1 |
| England League 2 | 2022/09/17 14:00 | Leyton Orient v Walsall | W | 1-0 |
| England League 2 | 2022/09/13 18:45 | Rochdale v Leyton Orient | W | 0-1 |
| England League 2 | 2022/09/03 14:00 | Leyton Orient v Tranmere | W | 2-0 |
Away History
| England Premier League 2 | 2022/10/15 11:00 | Chelsea U21 v Man Utd U21 | D | 3-3 |
| England Premier League 2 | 2022/10/08 15:00 | West Ham U21 v Chelsea U21 | W | 0-1 |
| England EFL Trophy | 2022/10/04 18:45 | Oxford Utd v Chelsea U21 | W | 1-2 |
| England Premier League 2 | 2022/10/01 11:00 | Chelsea U21 v Leicester U21 | D | 2-2 |
| England Premier League 2 | 2022/09/17 13:00 | Crystal Palace U21 v Chelsea U21 | D | 3-3 |
| England Premier League 2 | 2022/09/03 11:00 | Everton U21 v Chelsea U21 | W | 0-2 |
| England EFL Trophy | 2022/08/31 18:45 | Sutton Utd v Chelsea U21 | L | 1-0 |
| England Premier League 2 | 2022/08/26 18:00 | Chelsea U21 v Man City U21 | D | 2-2 |