| 04 May 2019 | | Chislehurst and West Kent Second XI v Shooters Hill Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 04 May 2019 | | Leeds and Broomfield Second XI v Bapchild Second XI | Burberry Lane, Leeds | Results |
| 11 May 2019 | | Ashford Town Second XI v Chislehurst and West Kent Second XI | Stacians Park, Ashford | Results |
| 11 May 2019 | | Bapchild Second XI v Leeds and Broomfield Second XI | Radfield Hill, Bapchild | Results |
| 11 May 2019 | | Cowdrey Second XI v Cobham Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 11 May 2019 | | Downham and Bellingham Second XI v Bromley Town Second XI | Rangefield Road, Downham | Results |
| 11 May 2019 | | Shooters Hill Second XI v High Halstow Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 18 May 2019 | | Bromley Town Second XI v Shooters Hill Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 18 May 2019 | | Chislehurst and West Kent Second XI v Downham and Bellingham Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 18 May 2019 | | Cobham Second XI v Bapchild Second XI | Cobham Sports Ground, Cobham | Results |
| 18 May 2019 | | High Halstow Second XI v Cowdrey Second XI | Rayners Meadow, High Halstow | Results |
| 18 May 2019 | | Leeds and Broomfield Second XI v Ashford Town Second XI | Burberry Lane, Leeds | Results |
| 25 May 2019 | | Ashford Town Second XI v Bromley Town Second XI | Stacians Park, Ashford | Results |
| 25 May 2019 | | Bapchild Second XI v Chislehurst and West Kent Second XI | Radfield Hill, Bapchild | Results |
| 25 May 2019 | | Cobham Second XI v Leeds and Broomfield Second XI | Cobham Sports Ground, Cobham | Results |
| 25 May 2019 | | Cowdrey Second XI v Shooters Hill Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 25 May 2019 | | Downham and Bellingham Second XI v High Halstow Second XI | Rangefield Road, Downham | Results |
| 01 Jun 2019 | | Bromley Town Second XI v Bapchild Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 01 Jun 2019 | | Chislehurst and West Kent Second XI v Cobham Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 01 Jun 2019 | | High Halstow Second XI v Ashford Town Second XI | Rayners Meadow, High Halstow | Results |
| 01 Jun 2019 | | Leeds and Broomfield Second XI v Cowdrey Second XI | Burberry Lane, Leeds | Results |
| 01 Jun 2019 | | Shooters Hill Second XI v Downham and Bellingham Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 08 Jun 2019 | | Ashford Town Second XI v Downham and Bellingham Second XI | Stacians Park, Ashford | Results |
| 08 Jun 2019 | | Bapchild Second XI v Shooters Hill Second XI | Radfield Hill, Bapchild | Results |
| 08 Jun 2019 | | Cobham Second XI v High Halstow Second XI | Cobham Sports Ground, Cobham | Results |
| 08 Jun 2019 | | Cowdrey Second XI v Chislehurst and West Kent Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 08 Jun 2019 | | Leeds and Broomfield Second XI v Bromley Town Second XI | Burberry Lane, Leeds | Results |
| 15 Jun 2019 | | Bromley Town Second XI v Cobham Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 15 Jun 2019 | | Chislehurst and West Kent Second XI v Leeds and Broomfield Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 15 Jun 2019 | | Downham and Bellingham Second XI v Cowdrey Second XI | Rangefield Road, Downham | Results |
| 15 Jun 2019 | | High Halstow Second XI v Bapchild Second XI | Rayners Meadow, High Halstow | Results |
| 15 Jun 2019 | | Shooters Hill Second XI v Ashford Town Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 22 Jun 2019 | | Ashford Town Second XI v Cobham Second XI | Stacians Park, Ashford | Results |
| 22 Jun 2019 | | Bapchild Second XI v Cowdrey Second XI | Radfield Hill, Bapchild | Results |
| 22 Jun 2019 | | Downham and Bellingham Second XI v Leeds and Broomfield Second XI | Rangefield Road, Downham | Results |
| 22 Jun 2019 | | High Halstow Second XI v Bromley Town Second XI | Rayners Meadow, High Halstow | Results |
| 22 Jun 2019 | | Shooters Hill Second XI v Chislehurst and West Kent Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 29 Jun 2019 | | Bapchild Second XI v Downham and Bellingham Second XI | Radfield Hill, Bapchild | Results |
| 29 Jun 2019 | | Chislehurst and West Kent Second XI v Bromley Town Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 29 Jun 2019 | | Cobham Second XI v Shooters Hill Second XI | Cobham Sports Ground, Cobham | Results |
| 29 Jun 2019 | | Cowdrey Second XI v Ashford Town Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 29 Jun 2019 | | Leeds and Broomfield Second XI v High Halstow Second XI | Burberry Lane, Leeds | Results |
| 06 Jul 2019 | | Ashford Town Second XI v Bapchild Second XI | Stacians Park, Ashford | Results |
| 06 Jul 2019 | | Bromley Town Second XI v Cowdrey Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 06 Jul 2019 | | Downham and Bellingham Second XI v Cobham Second XI | Rangefield Road, Downham | Results |
| 06 Jul 2019 | | High Halstow Second XI v Chislehurst and West Kent Second XI | Rayners Meadow, High Halstow | Results |
| 06 Jul 2019 | | Shooters Hill Second XI v Leeds and Broomfield Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 13 Jul 2019 | | Bromley Town Second XI v Downham and Bellingham Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 13 Jul 2019 | | Chislehurst and West Kent Second XI v Ashford Town Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 13 Jul 2019 | | Cobham Second XI v Cowdrey Second XI | Cobham Sports Ground, Cobham | Results |
| 13 Jul 2019 | | High Halstow Second XI v Shooters Hill Second XI | Rayners Meadow, High Halstow | Results |
| 20 Jul 2019 | | Ashford Town Second XI v Leeds and Broomfield Second XI | Stacians Park, Ashford | Results |
| 20 Jul 2019 | | Bapchild Second XI v Cobham Second XI | Radfield Hill, Bapchild | Results |
| 20 Jul 2019 | | Cowdrey Second XI v High Halstow Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 20 Jul 2019 | | Downham and Bellingham Second XI v Chislehurst and West Kent Second XI | Rangefield Road, Downham | Results |
| 20 Jul 2019 | | Shooters Hill Second XI v Bromley Town Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 27 Jul 2019 | | Bromley Town Second XI v Ashford Town Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 27 Jul 2019 | | Chislehurst and West Kent Second XI v Bapchild Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 27 Jul 2019 | | High Halstow Second XI v Downham and Bellingham Second XI | Rayners Meadow, High Halstow | Results |
| 27 Jul 2019 | | Leeds and Broomfield Second XI v Cobham Second XI | Burberry Lane, Leeds | Results |
| 27 Jul 2019 | | Shooters Hill Second XI v Cowdrey Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 03 Aug 2019 | | Ashford Town Second XI v High Halstow Second XI | Stacians Park, Ashford | Results |
| 03 Aug 2019 | | Bapchild Second XI v Bromley Town Second XI | Radfield Hill, Bapchild | Results |
| 03 Aug 2019 | | Cobham Second XI v Chislehurst and West Kent Second XI | Cobham Sports Ground, Cobham | Results |
| 03 Aug 2019 | | Cowdrey Second XI v Leeds and Broomfield Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 03 Aug 2019 | | Downham and Bellingham Second XI v Shooters Hill Second XI | Rangefield Road, Downham | Results |
| 10 Aug 2019 | | Bromley Town Second XI v Leeds and Broomfield Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 10 Aug 2019 | | Chislehurst and West Kent Second XI v Cowdrey Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 10 Aug 2019 | | Downham and Bellingham Second XI v Ashford Town Second XI | Rangefield Road, Downham | Results |
| 10 Aug 2019 | | High Halstow Second XI v Cobham Second XI | Rayners Meadow, High Halstow | Results |
| 10 Aug 2019 | | Shooters Hill Second XI v Bapchild Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 17 Aug 2019 | | Ashford Town Second XI v Shooters Hill Second XI | Stacians Park, Ashford | Results |
| 17 Aug 2019 | | Bapchild Second XI v High Halstow Second XI | Radfield Hill, Bapchild | Results |
| 17 Aug 2019 | | Cobham Second XI v Bromley Town Second XI | Cobham Sports Ground, Cobham | Results |
| 17 Aug 2019 | | Cowdrey Second XI v Downham and Bellingham Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 17 Aug 2019 | | Leeds and Broomfield Second XI v Chislehurst and West Kent Second XI | Burberry Lane, Leeds | Results |
| 24 Aug 2019 | | Bromley Town Second XI v High Halstow Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 24 Aug 2019 | | Cobham Second XI v Ashford Town Second XI | Cobham Sports Ground, Cobham | Results |
| 24 Aug 2019 | | Cowdrey Second XI v Bapchild Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 24 Aug 2019 | | Leeds and Broomfield Second XI v Downham and Bellingham Second XI | Burberry Lane, Leeds | Results |
| 31 Aug 2019 | | Ashford Town Second XI v Cowdrey Second XI | Stacians Park, Ashford | Results |
| 31 Aug 2019 | | Bromley Town Second XI v Chislehurst and West Kent Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 31 Aug 2019 | | Downham and Bellingham Second XI v Bapchild Second XI | Rangefield Road, Downham | Results |
| 31 Aug 2019 | | High Halstow Second XI v Leeds and Broomfield Second XI | Rayners Meadow, High Halstow | Results |
| 31 Aug 2019 | | Shooters Hill Second XI v Cobham Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 07 Sep 2019 | | Bapchild Second XI v Ashford Town Second XI | Radfield Hill, Bapchild | Results |
| 07 Sep 2019 | | Chislehurst and West Kent Second XI v High Halstow Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 07 Sep 2019 | | Cobham Second XI v Downham and Bellingham Second XI | Cobham Sports Ground, Cobham | Results |
| 07 Sep 2019 | | Cowdrey Second XI v Bromley Town Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 07 Sep 2019 | | Leeds and Broomfield Second XI v Shooters Hill Second XI | Burberry Lane, Leeds | Results |
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