16/05 - 20:00
| 2023/03/21 | Braintree Town |  | 2-0 |  | Concord Rangers |
| 2023/02/27 | Chelmsford City |  | 0-1 | | Braintree Town | ||||
| 2023/02/28 | Concord Rangers | | 1-1 (5-4 pens) |  | Hornchurch |
| 2023/01/31 | Hornchurch | | 4-1 |  | Billericay Town | ||||
| 2023/02/06 | Chelmsford City | | 4-0 |  | Witham Town | ||||
| 2023/02/07 | Colchester U21 |  | 2-3 | | Braintree Town | ||||
| 2023/02/21 | Canvey Island |  | 0-0 (2-3 pens) | | Concord Rangers |
| 2023/01/04 | Colchester U21 | | 10-0 |  | Saffron Walden Town | ||||
| 2023/01/09 | Chelmsford City | | 5-1 |  | Coggeshall Town | ||||
| Romford |  | 1-3 | | Hornchurch | |||||
| 2023/01/10 | Bowers & Pitsea |  | 1-2 | | Canvey Island | ||||
| 2023/01/13 | Harlow Town |  | WO | | Billericay Town | ||||
| 2023/01/24 | Concord Rangers | | 1-3 |  | Grays Athletic | ||||
| 2023/01/25 | Southend United U21 |  | WO | | Braintree Town | ||||
| 2023/01/31 | Witham Town | | 3-1 |  | East Thurrock |
