| 29 Apr 2023 | | Dulwich Sixth XI v Ex-Blues Second XI | Turney Road, Dulwich | Results |
| 29 Apr 2023 | | Bromley Common Fifth XI v Catford and Cyphers Fourth XI | The Acorns, Bromley | Results |
| 29 Apr 2023 | | Old Roan Third XI v Alleyn Fourth XI | John Roan School Playing Fields, Blackheath | Results |
| 06 May 2023 | | Bromley Common Fifth XI v Bexleyheath Fifth XI | Honourable Artillery Company Ground, Finsbury | Results |
| 06 May 2023 | | Catford and Cyphers Fourth XI v Beckenham Sixth XI | St Dunstan's College Ground, Catford | Results |
| 06 May 2023 | | Old Roan Third XI v Ex-Blues Second XI | Honourable Artillery Company Ground, Finsbury | Results |
| 06 May 2023 | | Old Wilsonians Fourth XI v Alleyn Fourth XI | Hawes Down School Sports Ground, Hayes Hill, Hayes | Results |
| 13 May 2023 | | Alleyn Fourth XI v Bexleyheath Fifth XI | Old Alleynians Ground, Dulwich Common | Results |
| 13 May 2023 | | Beckenham Sixth XI v Old Wilsonians Fourth XI | Forster Memorial Park, Sydenham | Results |
| 13 May 2023 | | Dulwich Sixth XI v Old Roan Third XI | Turney Road, Dulwich | Results |
| 13 May 2023 | | Ex-Blues Second XI v Catford and Cyphers Fourth XI | Pickhurst Rise, West Wickham | Results |
| 20 May 2023 | | Beckenham Sixth XI v Old Roan Third XI | Forster Memorial Park, Sydenham | Results |
| 20 May 2023 | | Bexleyheath Fifth XI v Old Wilsonians Fourth XI | Honourable Artillery Company Ground, Finsbury | Results |
| 20 May 2023 | | Catford and Cyphers Fourth XI v Dulwich Sixth XI | St Dunstan's College Ground, Catford | Results |
| 20 May 2023 | | Ex-Blues Second XI v Alleyn Fourth XI | Pickhurst Rise, West Wickham | Results |
| 27 May 2023 | | Alleyn Fourth XI v Bromley Common Fifth XI | Old Alleynians Ground, Dulwich Common | Results |
| 27 May 2023 | | Beckenham Sixth XI v Catford and Cyphers Fourth XI | Forster Memorial Park, Sydenham | Results |
| 27 May 2023 | | Old Wilsonians Fourth XI v Bexleyheath Fifth XI | Hawes Down School Sports Ground, Hayes Hill, Hayes | Results |
| 03 Jun 2023 | | Bexleyheath Fifth XI v Beckenham Sixth XI | Honourable Artillery Company Ground, Finsbury | Results |
| 03 Jun 2023 | | Catford and Cyphers Fourth XI v Old Roan Third XI | St Dunstan's College Ground, Catford | Results |
| 03 Jun 2023 | | Dulwich Sixth XI v Alleyn Fourth XI | Turney Road, Dulwich | Results |
| 03 Jun 2023 | | Ex-Blues Second XI v Bromley Common Fifth XI | Pickhurst Rise, West Wickham | Results |
| 10 Jun 2023 | | Alleyn Fourth XI v Old Roan Third XI | Old Alleynians Ground, Dulwich Common | Results |
| 10 Jun 2023 | | Beckenham Sixth XI v Ex-Blues Second XI | Forster Memorial Park, Sydenham | Results |
| 10 Jun 2023 | | Old Wilsonians Fourth XI v Dulwich Sixth XI | Hawes Down School Sports Ground, Hayes Hill, Hayes | Results |
| 17 Jun 2023 | | Bexleyheath Fifth XI v Alleyn Fourth XI | Honourable Artillery Company Ground, Finsbury | Results |
| 17 Jun 2023 | | Bromley Common Fifth XI v Dulwich Sixth XI | Honourable Artillery Company Ground, Finsbury | Results |
| 17 Jun 2023 | | Old Roan Third XI v Catford and Cyphers Fourth XI | Honourable Artillery Company Ground, Finsbury | Results |
| 17 Jun 2023 | | Old Wilsonians Fourth XI v Ex-Blues Second XI | Hawes Down School Sports Ground, Hayes Hill, Hayes | Results |
| 24 Jun 2023 | | Alleyn Fourth XI v Beckenham Sixth XI | Old Alleynians Ground, Dulwich Common | Results |
| 24 Jun 2023 | | Dulwich Sixth XI v Old Wilsonians Fourth XI | Turney Road, Dulwich | Results |
| 24 Jun 2023 | | Ex-Blues Second XI v Bexleyheath Fifth XI | Pickhurst Rise, West Wickham | Results |
| 24 Jun 2023 | | Old Roan Third XI v Bromley Common Fifth XI | Charlton Park, Charlton | Results |
| 01 Jul 2023 | | Beckenham Sixth XI v Dulwich Sixth XI | Forster Memorial Park, Sydenham | Results |
| 01 Jul 2023 | | Bexleyheath Fifth XI v Catford and Cyphers Fourth XI | Honourable Artillery Company Ground, Finsbury | Results |
| 01 Jul 2023 | | Bromley Common Fifth XI v Alleyn Fourth XI | Honourable Artillery Company Ground, Finsbury | Results |
| 01 Jul 2023 | | Old Wilsonians Fourth XI v Old Roan Third XI | Hawes Down School Sports Ground, Hayes Hill, Hayes | Results |
| 08 Jul 2023 | | Alleyn Fourth XI v Catford and Cyphers Fourth XI | Old Alleynians Ground, Dulwich Common | Results |
| 08 Jul 2023 | | Dulwich Sixth XI v Bromley Common Fifth XI | Turney Road, Dulwich | Results |
| 08 Jul 2023 | | Ex-Blues Second XI v Old Wilsonians Fourth XI | Pickhurst Rise, West Wickham | Results |
| 08 Jul 2023 | | Old Roan Third XI v Beckenham Sixth XI | Charlton Park, Charlton | Results |
| 15 Jul 2023 | | Bexleyheath Fifth XI v Dulwich Sixth XI | Honourable Artillery Company Ground, Finsbury | Results |
| 15 Jul 2023 | | Bromley Common Fifth XI v Old Roan Third XI | Honourable Artillery Company Ground, Finsbury | Results |
| 15 Jul 2023 | | Catford and Cyphers Fourth XI v Ex-Blues Second XI | St Dunstan's College Ground, Catford | Results |
| 15 Jul 2023 | | Old Wilsonians Fourth XI v Beckenham Sixth XI | Hawes Down School Sports Ground, Hayes Hill, Hayes | Results |
| 22 Jul 2023 | | Alleyn Fourth XI v Ex-Blues Second XI | Old Alleynians Ground, Dulwich Common | Results |
| 22 Jul 2023 | | Beckenham Sixth XI v Bromley Common Fifth XI | Forster Memorial Park, Sydenham | Results |
| 22 Jul 2023 | | Dulwich Sixth XI v Catford and Cyphers Fourth XI | Turney Road, Dulwich | Results |
| 22 Jul 2023 | | Old Roan Third XI v Bexleyheath Fifth XI | Harvey Road, Blackheath | Results |
| 29 Jul 2023 | | Bexleyheath Fifth XI v Bromley Common Fifth XI | Honourable Artillery Company Ground, Finsbury | Results |
| 29 Jul 2023 | | Catford and Cyphers Fourth XI v Old Wilsonians Fourth XI | St Dunstan's College Ground, Catford | Results |
| 29 Jul 2023 | | Ex-Blues Second XI v Dulwich Sixth XI | Pickhurst Rise, West Wickham | Results |
| 05 Aug 2023 | | Alleyn Fourth XI v Dulwich Sixth XI | Old Alleynians Ground, Dulwich Common | Results |
| 05 Aug 2023 | | Beckenham Sixth XI v Bexleyheath Fifth XI | Forster Memorial Park, Sydenham | Results |
| 05 Aug 2023 | | Bromley Common Fifth XI v Ex-Blues Second XI | The Acorns, Bromley | Results |
| 05 Aug 2023 | | Old Wilsonians Fourth XI v Catford and Cyphers Fourth XI | Hawes Down School Sports Ground, Hayes Hill, Hayes | Results |
| 12 Aug 2023 | | Bexleyheath Fifth XI v Old Roan Third XI | Honourable Artillery Company Ground, Finsbury | Results |
| 12 Aug 2023 | | Bromley Common Fifth XI v Old Wilsonians Fourth XI | Honourable Artillery Company Ground, Finsbury | Results |
| 12 Aug 2023 | | Catford and Cyphers Fourth XI v Alleyn Fourth XI | St Dunstan's College Ground, Catford | Results |
| 12 Aug 2023 | | Dulwich Sixth XI v Beckenham Sixth XI | Turney Road, Dulwich | Results |
| 19 Aug 2023 | | Alleyn Fourth XI v Old Wilsonians Fourth XI | Old Alleynians Ground, Dulwich Common | Results |
| 19 Aug 2023 | | Catford and Cyphers Fourth XI v Bexleyheath Fifth XI | St Dunstan's College Ground, Catford | Results |
| 19 Aug 2023 | | Ex-Blues Second XI v Old Roan Third XI | Pickhurst Rise, West Wickham | Results |
| 26 Aug 2023 | | Beckenham Sixth XI v Alleyn Fourth XI | Forster Memorial Park, Sydenham | Results |
| 26 Aug 2023 | | Bexleyheath Fifth XI v Ex-Blues Second XI | Honourable Artillery Company Ground, Finsbury | Results |
| 26 Aug 2023 | | Old Wilsonians Fourth XI v Bromley Common Fifth XI | Hawes Down School Sports Ground, Hayes Hill, Hayes | Results |
| 02 Sep 2023 | | Catford and Cyphers Fourth XI v Bromley Common Fifth XI | St Dunstan's College Ground, Catford | Results |
| 02 Sep 2023 | | Dulwich Sixth XI v Bexleyheath Fifth XI | Turney Road, Dulwich | Results |
| 02 Sep 2023 | | Ex-Blues Second XI v Beckenham Sixth XI | Pickhurst Rise, West Wickham | Results |
| 02 Sep 2023 | | Old Roan Third XI v Old Wilsonians Fourth XI | Honourable Artillery Company Ground, Finsbury | Results |
| 09 Sep 2023 | | Bromley Common Fifth XI v Beckenham Sixth XI | The Acorns, Bromley | Results |
| 09 Sep 2023 | | Old Roan Third XI v Dulwich Sixth XI | John Roan School Playing Fields, Blackheath | Results |
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