Knockout - fixtures : click on result for match card
| Home Team | Result | Away Team | Date | Time | Status |
|---|---|---|---|---|---|
| Brentwood | 4 - 0 | Braintree A | Tue 17 Oct 23 | 19:30 | OV |
| Maldon | 2½ - 1½ | Colchester A | Wed 18 Oct 23 | 19:30 | OV |
| Witham A | 4 - 0 | Chelmsford B | Wed 25 Oct 23 | 19:30 | OV |
| Witham B | 0 - 4 | Chelmsford A | Wed 25 Oct 23 | 19:30 | OV |
| Colchester B | 3½ - ½ | Braintree B | Wed 22 Nov 23 | 19:30 | OV |
| Brentwood | 0 - 0 | Week 27th Nov 2023 | 19:30 | OU | |
| Colchester B | 0 - 0 | Week 27th Nov 2023 | 19:30 | OU | |
| Maldon | 0 - 0 | Week 27th Nov 2023 | 19:30 | OU | |
| Chelmsford A | 2½ - 1½ | Witham A | Mon 27 Nov 23 | 19:30 | OV |
| Chelmsford A | 3½ - ½ | Colchester B | Mon 15 Jan 24 | 19:30 | OV |
| Brentwood | 3 - 1 | Maldon | Tue 16 Jan 24 | 19:30 | OV |
| Chelmsford A | 1½ - 2½ | Brentwood | Mon 26 Feb 24 | 19:30 | OU |