Home History
| England - National League South | 2021/11/20 15:00 | Tonbridge Angels v Chelmsford | D | 1-1 |
| England - National League South | 2021/11/13 15:00 | Chelmsford v Hemel Hempstead | L | 1-2 |
| England - National League South | 2021/11/06 15:00 | Eastbourne Borough v Chelmsford | L | 2-1 |
| England - National League South | 2021/10/30 14:00 | Chelmsford v Havant and W | L | 2-3 |
| England - National League South | 2021/10/25 18:45 | Chelmsford v Dartford | D | 0-0 |
| England - National League South | 2021/10/23 14:00 | Oxford City v Chelmsford | D | 1-1 |
| England - FA Cup - Kvalifikation | 2021/10/16 14:00 | Harrow Borough v Chelmsford | L | 4-2 |
| England - National League South | 2021/10/09 14:00 | Hampton & Richmond v Chelmsford | L | 4-2 |
Away History
| England - Isthmian Premier Division | 2021/11/23 19:45 | Wingate & Finchley v Cheshunt | W | 1-3 |
| England - Isthmian Premier Division | 2021/11/20 15:00 | Worthing v Cheshunt | W | 1-2 |
| England - FA Trophy | 2021/11/13 15:00 | Cheshunt v Berkhamsted | W | 1-0 |
| England - Isthmian Premier Division | 2021/11/09 19:45 | Leatherhead v Cheshunt | W | 1-2 |
| England - Isthmian Premier Division | 2021/11/06 15:00 | Cheshunt v Folkestone Invicta | D | 0-0 |
| England - FA Trophy | 2021/10/30 14:00 | Corinthian Casuals v Cheshunt | W | 0-1 |
| England - Isthmian Premier Division | 2021/10/23 14:00 | Cheshunt v Cray Wanderers | W | 4-0 |
| England - Isthmian Premier Division | 2021/10/19 18:45 | Horsham v Cheshunt | W | 0-2 |