| 18 Jul 2020 | | Belhus Second XI v Old Southendian and Southchurch Second XI | The Village Green, North Stifford | Results |
| 18 Jul 2020 | | Benfleet Second XI v Hadleigh and Thundersley Second XI | Woodside Park, Thundersley | Results |
| 18 Jul 2020 | | Horndon-on-the-Hill Second XI v Billericay Second XI | The Recreation Ground, Horndon-on-the-Hill | Results |
| 18 Jul 2020 | | Southend-on-Sea and Ekco Monarchs and Trojans Second XI v Leigh-on-Sea Second XI | Southchurch Park, Southend-on-Sea | Results |
| 18 Jul 2020 | | Westcliff-on-Sea Second XI v Wickford Second XI | Chalkwell Park, Westcliff-on-Sea | Results |
| 25 Jul 2020 | | Benfleet Second XI v Belhus Second XI | Woodside Park, Thundersley | Results |
| 25 Jul 2020 | | Billericay Second XI v Westcliff-on-Sea Second XI | The Toby Howe Cricket Ground, Billericay | Results |
| 25 Jul 2020 | | Hadleigh and Thundersley Second XI v Horndon-on-the-Hill Second XI | John H Burrows Recreation Ground, Hadleigh | Results |
| 25 Jul 2020 | | Old Southendian and Southchurch Second XI v Leigh-on-Sea Second XI | Garon Park, Southend-on-Sea | Results |
| 25 Jul 2020 | | Wickford Second XI v Southend-on-Sea and Ekco Monarchs and Trojans Second XI | Dick Patmore Memorial Ground, Wickford | Results |
| 01 Aug 2020 | | Horndon-on-the-Hill Second XI v Belhus Second XI | The Recreation Ground, Horndon-on-the-Hill | Results |
| 01 Aug 2020 | | Leigh-on-Sea Second XI v Benfleet Second XI | Chalkwell Park, Westcliff-on-Sea | Results |
| 01 Aug 2020 | | Southend-on-Sea and Ekco Monarchs and Trojans Second XI v Old Southendian and Southchurch Second XI | Southchurch Park, Southend-on-Sea | Results |
| 01 Aug 2020 | | Westcliff-on-Sea Second XI v Hadleigh and Thundersley Second XI | Chalkwell Park, Westcliff-on-Sea | Results |
| 01 Aug 2020 | | Wickford Second XI v Billericay Second XI | Dick Patmore Memorial Ground, Wickford | Results |
| 08 Aug 2020 | | Belhus Second XI v Westcliff-on-Sea Second XI | The Village Green, North Stifford | Results |
| 08 Aug 2020 | | Benfleet Second XI v Old Southendian and Southchurch Second XI | Woodside Park, Thundersley | Results |
| 08 Aug 2020 | | Hadleigh and Thundersley Second XI v Wickford Second XI | John H Burrows Recreation Ground, Hadleigh | Results |
| 08 Aug 2020 | | Horndon-on-the-Hill Second XI v Leigh-on-Sea Second XI | The Recreation Ground, Horndon-on-the-Hill | Results |
| 08 Aug 2020 | | Southend-on-Sea and Ekco Monarchs and Trojans Second XI v Billericay Second XI | Southchurch Park, Southend-on-Sea | Results |
| 15 Aug 2020 | | Billericay Second XI v Hadleigh and Thundersley Second XI | The Toby Howe Cricket Ground, Billericay | Results |
| 15 Aug 2020 | | Leigh-on-Sea Second XI v Westcliff-on-Sea Second XI | Chalkwell Park, Westcliff-on-Sea | Results |
| 15 Aug 2020 | | Old Southendian and Southchurch Second XI v Horndon-on-the-Hill Second XI | Garon Park, Southend-on-Sea | Results |
| 15 Aug 2020 | | Southend-on-Sea and Ekco Monarchs and Trojans Second XI v Benfleet Second XI | Southchurch Park, Southend-on-Sea | Results |
| 15 Aug 2020 | | Wickford Second XI v Belhus Second XI | Dick Patmore Memorial Ground, Wickford | Results |
| 22 Aug 2020 | | Belhus Second XI v Billericay Second XI | The Village Green, North Stifford | Results |
| 22 Aug 2020 | | Horndon-on-the-Hill Second XI v Benfleet Second XI | The Recreation Ground, Horndon-on-the-Hill | Results |
| 22 Aug 2020 | | Leigh-on-Sea Second XI v Wickford Second XI | Chalkwell Park, Westcliff-on-Sea | Results |
| 22 Aug 2020 | | Southend-on-Sea and Ekco Monarchs and Trojans Second XI v Hadleigh and Thundersley Second XI | Southchurch Park, Southend-on-Sea | Results |
| 22 Aug 2020 | | Westcliff-on-Sea Second XI v Old Southendian and Southchurch Second XI | Chalkwell Park, Westcliff-on-Sea | Results |
| 29 Aug 2020 | | Belhus Second XI v Hadleigh and Thundersley Second XI | The Village Green, North Stifford | Results |
| 29 Aug 2020 | | Benfleet Second XI v Westcliff-on-Sea Second XI | Woodside Park, Thundersley | Results |
| 29 Aug 2020 | | Billericay Second XI v Leigh-on-Sea Second XI | The Toby Howe Cricket Ground, Billericay | Results |
| 29 Aug 2020 | | Old Southendian and Southchurch Second XI v Wickford Second XI | Garon Park, Southend-on-Sea | Results |
| 29 Aug 2020 | | Southend-on-Sea and Ekco Monarchs and Trojans Second XI v Horndon-on-the-Hill Second XI | Southchurch Park, Southend-on-Sea | Results |
| 05 Sep 2020 | | Billericay Second XI v Benfleet Second XI | The Toby Howe Cricket Ground, Billericay | Results |
| 05 Sep 2020 | | Hadleigh and Thundersley Second XI v Old Southendian and Southchurch Second XI | John H Burrows Recreation Ground, Hadleigh | Results |
| 05 Sep 2020 | | Horndon-on-the-Hill Second XI v Wickford Second XI | The Recreation Ground, Horndon-on-the-Hill | Results |
| 05 Sep 2020 | | Leigh-on-Sea Second XI v Belhus Second XI | Chalkwell Park, Westcliff-on-Sea | Results |
| 05 Sep 2020 | | Westcliff-on-Sea Second XI v Southend-on-Sea and Ekco Monarchs and Trojans Second XI | Chalkwell Park, Westcliff-on-Sea | Results |
| 12 Sep 2020 | | Belhus Second XI v Southend-on-Sea and Ekco Monarchs and Trojans Second XI | The Village Green, North Stifford | Results |
| 12 Sep 2020 | | Billericay Second XI v Old Southendian and Southchurch Second XI | The Toby Howe Cricket Ground, Billericay | Results |
| 12 Sep 2020 | | Horndon-on-the-Hill Second XI v Westcliff-on-Sea Second XI | The Recreation Ground, Horndon-on-the-Hill | Results |
| 12 Sep 2020 | | Leigh-on-Sea Second XI v Hadleigh and Thundersley Second XI | Chalkwell Park, Westcliff-on-Sea | Results |
| 12 Sep 2020 | | Wickford Second XI v Benfleet Second XI | Dick Patmore Memorial Ground, Wickford | Results |
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