Home History
| Club Friendly List | 2023/07/11 18:30 | Heybridge Swifts v Chelmsford | W | 1-3 |
| England National League South | 2023/05/02 18:30 | Chelmsford v St Albans | L | 0-1 |
| England National League South | 2023/04/29 14:00 | Chelmsford v Taunton Town | L | 1-2 |
| England National League South | 2023/04/22 14:00 | Hemel Hempstead v Chelmsford | D | 0-0 |
| England National League South | 2023/04/18 18:45 | Cheshunt v Chelmsford | W | 1-2 |
| England National League South | 2023/04/15 14:00 | Chelmsford v Hungerford Town | W | 5-1 |
| England National League South | 2023/04/10 14:00 | Oxford City v Chelmsford | L | 3-1 |
| England National League South | 2023/04/07 14:00 | Chelmsford v Farnborough | W | 3-2 |
Away History
| Club Friendly List | 2023/07/14 09:00 | Charlton v Leyton Orient | D | 1-1 |
| Club Friendly List | 2023/07/07 18:45 | Billericay Town v Leyton Orient | D | 0-0 |
| England League 2 | 2023/05/08 11:30 | Bradford v Leyton Orient | D | 1-1 |
| England League 2 | 2023/04/29 14:00 | Leyton Orient v Stockport | L | 0-3 |
| England League 2 | 2023/04/25 18:45 | Mansfield v Leyton Orient | W | 1-2 |
| England League 2 | 2023/04/22 14:00 | Leyton Orient v Crewe | W | 2-0 |
| England League 2 | 2023/04/18 18:45 | Gillingham v Leyton Orient | L | 2-0 |
| England League 2 | 2023/04/15 14:00 | Sutton Utd v Leyton Orient | W | 0-2 |