| 29 Apr 2023 | | High Halstow Second XI v LESSA Christ Church | Rayners Meadow, High Halstow | Results |
| 06 May 2023 | | Barbados Overseas Cricket Association v Chislehurst and West Kent Second XI | Turney Road, Dulwich | Results |
| 06 May 2023 | | Bromley Town Second XI v LESSA Christ Church | Hayes Lane Cricket Ground, Bromley | Results |
| 06 May 2023 | | Kings Hill Second XI v Wickham Park | Kings Hill Oval, West Malling | Results |
| 06 May 2023 | | Old Roan v High Halstow Second XI | John Roan School Playing Fields, Blackheath | Results |
| 06 May 2023 | | Roebucks Second XI v Tonbridge Second XI | Burton Pynsent House, Hayes | Results |
| 13 May 2023 | | Barbados Overseas Cricket Association v Kings Hill Second XI | Turney Road, Dulwich | Results |
| 13 May 2023 | | High Halstow Second XI v Chislehurst and West Kent Second XI | Rayners Meadow, High Halstow | Results |
| 13 May 2023 | | LESSA Christ Church v Old Roan | EDF Energy Ground, New Eltham | Results |
| 13 May 2023 | | Tonbridge Second XI v Bromley Town Second XI | Poplar Meadow, Tonbridge | Results |
| 13 May 2023 | | Wickham Park v Roebucks Second XI | Wickham Park Sports Club Ground, West Wickham | Results |
| 20 May 2023 | | Bromley Town Second XI v High Halstow Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 20 May 2023 | | Kings Hill Second XI v Tonbridge Second XI | Kings Hill Oval, West Malling | Results |
| 20 May 2023 | | Old Roan v Chislehurst and West Kent Second XI | John Roan School Playing Fields, Blackheath | Results |
| 20 May 2023 | | Roebucks Second XI v LESSA Christ Church | Burton Pynsent House, Hayes | Results |
| 20 May 2023 | | Wickham Park v Barbados Overseas Cricket Association | Wickham Park Sports Club Ground, West Wickham | Results |
| 27 May 2023 | | Barbados Overseas Cricket Association v Old Roan | Turney Road, Dulwich | Results |
| 27 May 2023 | | Chislehurst and West Kent Second XI v Bromley Town Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 27 May 2023 | | High Halstow Second XI v Roebucks Second XI | Rayners Meadow, High Halstow | Results |
| 27 May 2023 | | LESSA Christ Church v Kings Hill Second XI | EDF Energy Ground, New Eltham | Results |
| 27 May 2023 | | Tonbridge Second XI v Wickham Park | Poplar Meadow, Tonbridge | Results |
| 03 Jun 2023 | | Bromley Town Second XI v Barbados Overseas Cricket Association | Hayes Lane Cricket Ground, Bromley | Results |
| 03 Jun 2023 | | Kings Hill Second XI v Chislehurst and West Kent Second XI | Kings Hill Oval, West Malling | Results |
| 03 Jun 2023 | | Roebucks Second XI v Old Roan | Burton Pynsent House, Hayes | Results |
| 03 Jun 2023 | | Tonbridge Second XI v LESSA Christ Church | Poplar Meadow, Tonbridge | Results |
| 03 Jun 2023 | | Wickham Park v High Halstow Second XI | Wickham Park Sports Club Ground, West Wickham | Results |
| 10 Jun 2023 | | Barbados Overseas Cricket Association v Tonbridge Second XI | Turney Road, Dulwich | Results |
| 10 Jun 2023 | | Chislehurst and West Kent Second XI v Roebucks Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 10 Jun 2023 | | High Halstow Second XI v Kings Hill Second XI | Rayners Meadow, High Halstow | Results |
| 10 Jun 2023 | | LESSA Christ Church v Wickham Park | EDF Energy Ground, New Eltham | Results |
| 10 Jun 2023 | | Old Roan v Bromley Town Second XI | John Roan School Playing Fields, Blackheath | Results |
| 17 Jun 2023 | | Barbados Overseas Cricket Association v High Halstow Second XI | Turney Road, Dulwich | Results |
| 17 Jun 2023 | | Bromley Town Second XI v Wickham Park | Hayes Lane Cricket Ground, Bromley | Results |
| 17 Jun 2023 | | Chislehurst and West Kent Second XI v LESSA Christ Church | West Kent Cricket Club Ground, Chislehurst | Results |
| 17 Jun 2023 | | Old Roan v Tonbridge Second XI | John Roan School Playing Fields, Blackheath | Results |
| 17 Jun 2023 | | Roebucks Second XI v Kings Hill Second XI | Burton Pynsent House, Hayes | Results |
| 24 Jun 2023 | | Kings Hill Second XI v Old Roan | Kings Hill Oval, West Malling | Results |
| 24 Jun 2023 | | LESSA Christ Church v Barbados Overseas Cricket Association | EDF Energy Ground, New Eltham | Results |
| 24 Jun 2023 | | Roebucks Second XI v Bromley Town Second XI | Burton Pynsent House, Hayes | Results |
| 24 Jun 2023 | | Tonbridge Second XI v High Halstow Second XI | Poplar Meadow, Tonbridge | Results |
| 24 Jun 2023 | | Wickham Park v Chislehurst and West Kent Second XI | Wickham Park Sports Club Ground, West Wickham | Results |
| 01 Jul 2023 | | Barbados Overseas Cricket Association v Roebucks Second XI | Turney Road, Dulwich | Results |
| 01 Jul 2023 | | Bromley Town Second XI v Kings Hill Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 01 Jul 2023 | | Chislehurst and West Kent Second XI v Tonbridge Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 01 Jul 2023 | | Old Roan v Wickham Park | John Roan School Playing Fields, Blackheath | Results |
| 08 Jul 2023 | | Chislehurst and West Kent Second XI v Barbados Overseas Cricket Association | West Kent Cricket Club Ground, Chislehurst | Results |
| 08 Jul 2023 | | High Halstow Second XI v Old Roan | Rayners Meadow, High Halstow | Results |
| 08 Jul 2023 | | LESSA Christ Church v Bromley Town Second XI | EDF Energy Ground, New Eltham | Results |
| 08 Jul 2023 | | Tonbridge Second XI v Roebucks Second XI | Poplar Meadow, Tonbridge | Results |
| 08 Jul 2023 | | Wickham Park v Kings Hill Second XI | Wickham Park Sports Club Ground, West Wickham | Results |
| 15 Jul 2023 | | Bromley Town Second XI v Tonbridge Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 15 Jul 2023 | | Chislehurst and West Kent Second XI v High Halstow Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 15 Jul 2023 | | Kings Hill Second XI v Barbados Overseas Cricket Association | Kings Hill Oval, West Malling | Results |
| 15 Jul 2023 | | Old Roan v LESSA Christ Church | John Roan School Playing Fields, Blackheath | Results |
| 15 Jul 2023 | | Roebucks Second XI v Wickham Park | Burton Pynsent House, Hayes | Results |
| 22 Jul 2023 | | Barbados Overseas Cricket Association v Wickham Park | Turney Road, Dulwich | Results |
| 22 Jul 2023 | | Chislehurst and West Kent Second XI v Old Roan | West Kent Cricket Club Ground, Chislehurst | Results |
| 22 Jul 2023 | | High Halstow Second XI v Bromley Town Second XI | Rayners Meadow, High Halstow | Results |
| 22 Jul 2023 | | LESSA Christ Church v Roebucks Second XI | EDF Energy Ground, New Eltham | Results |
| 22 Jul 2023 | | Tonbridge Second XI v Kings Hill Second XI | Poplar Meadow, Tonbridge | Results |
| 29 Jul 2023 | | Bromley Town Second XI v Chislehurst and West Kent Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 29 Jul 2023 | | Kings Hill Second XI v LESSA Christ Church | Kings Hill Oval, West Malling | Results |
| 29 Jul 2023 | | Old Roan v Barbados Overseas Cricket Association | John Roan School Playing Fields, Blackheath | Results |
| 29 Jul 2023 | | Roebucks Second XI v High Halstow Second XI | Burton Pynsent House, Hayes | Results |
| 29 Jul 2023 | | Wickham Park v Tonbridge Second XI | Wickham Park Sports Club Ground, West Wickham | Results |
| 05 Aug 2023 | | Barbados Overseas Cricket Association v Bromley Town Second XI | Turney Road, Dulwich | Results |
| 05 Aug 2023 | | Chislehurst and West Kent Second XI v Kings Hill Second XI | West Kent Cricket Club Ground, Chislehurst | Results |
| 05 Aug 2023 | | High Halstow Second XI v Wickham Park | Rayners Meadow, High Halstow | Results |
| 05 Aug 2023 | | LESSA Christ Church v Tonbridge Second XI | EDF Energy Ground, New Eltham | Results |
| 05 Aug 2023 | | Old Roan v Roebucks Second XI | John Roan School Playing Fields, Blackheath | Results |
| 12 Aug 2023 | | Bromley Town Second XI v Old Roan | Hayes Lane Cricket Ground, Bromley | Results |
| 12 Aug 2023 | | Kings Hill Second XI v High Halstow Second XI | Kings Hill Oval, West Malling | Results |
| 12 Aug 2023 | | Roebucks Second XI v Chislehurst and West Kent Second XI | Burton Pynsent House, Hayes | Results |
| 12 Aug 2023 | | Tonbridge Second XI v Barbados Overseas Cricket Association | Poplar Meadow, Tonbridge | Results |
| 12 Aug 2023 | | Wickham Park v LESSA Christ Church | Wickham Park Sports Club Ground, West Wickham | Results |
| 19 Aug 2023 | | High Halstow Second XI v Barbados Overseas Cricket Association | Rayners Meadow, High Halstow | Results |
| 19 Aug 2023 | | Kings Hill Second XI v Roebucks Second XI | Kings Hill Oval, West Malling | Results |
| 19 Aug 2023 | | LESSA Christ Church v Chislehurst and West Kent Second XI | EDF Energy Ground, New Eltham | Results |
| 19 Aug 2023 | | Tonbridge Second XI v Old Roan | Poplar Meadow, Tonbridge | Results |
| 19 Aug 2023 | | Wickham Park v Bromley Town Second XI | Wickham Park Sports Club Ground, West Wickham | Results |
| 26 Aug 2023 | | Barbados Overseas Cricket Association v LESSA Christ Church | Turney Road, Dulwich | Results |
| 26 Aug 2023 | | Bromley Town Second XI v Roebucks Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 26 Aug 2023 | | Chislehurst and West Kent Second XI v Wickham Park | West Kent Cricket Club Ground, Chislehurst | Results |
| 26 Aug 2023 | | High Halstow Second XI v Tonbridge Second XI | Rayners Meadow, High Halstow | Results |
| 26 Aug 2023 | | Old Roan v Kings Hill Second XI | John Roan School Playing Fields, Blackheath | Results |
| 02 Sep 2023 | | Kings Hill Second XI v Bromley Town Second XI | Kings Hill Oval, West Malling | Results |
| 02 Sep 2023 | | LESSA Christ Church v High Halstow Second XI | EDF Energy Ground, New Eltham | Results |
| 02 Sep 2023 | | Roebucks Second XI v Barbados Overseas Cricket Association | Burton Pynsent House, Hayes | Results |
| 02 Sep 2023 | | Tonbridge Second XI v Chislehurst and West Kent Second XI | Poplar Meadow, Tonbridge | Results |
| 02 Sep 2023 | | Wickham Park v Old Roan | Wickham Park Sports Club Ground, West Wickham | Results |
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