| 21 May 2023 | First Round | Blackheath v Three Bridges | The Rectory Field, Blackheath | Results |
| 21 May 2023 | First Round | Bromley v Banstead | Plaistow Lane, Bromley | Results |
| 21 May 2023 | First Round | Dartford v Upminster | Hesketh Park, Dartford | Results |
| 21 May 2023 | First Round | Harrow Town v Hertford | Harrow Town Sports Club Ground, Harrow | Results |
| 21 May 2023 | First Round | High Halstow v Hornchurch | Rayners Meadow, High Halstow | Results |
| 21 May 2023 | First Round | Hoddesdon v Sawston and Babraham | Lowfield, Hoddesdon | Results |
| 21 May 2023 | First Round | Hornsey v Winchmore Hill | Tivoli Road, Hornsey | Results |
| 21 May 2023 | First Round | Horsley and Send v Waltham | Twinn's Field, West Horsley | Results |
| 21 May 2023 | First Round | Hutton v Minster (Sheppey) | The Polo Field Ground, Hutton | Results |
| 14 May 2023 | First Round | Ickenham v Old Hamptonians | Oak Avenue, Ickenham | Results |
| 21 May 2023 | First Round | South Hampstead v Egham | Milverton Road, Willesden | Results |
| 21 May 2023 | First Round | Sunbury v North Middlesex | Kenton Court Meadow, Sunbury-on-Thames | Results |
| 21 May 2023 | First Round | Sutton v Paragon | Cheam Road, Sutton | Results |
| 21 May 2023 | First Round | Totteridge Millhillians v Enfield | Totteridge Green, Totteridge | Results |
| 21 May 2023 | First Round | Walton-on-Thames v High Wycombe | Ashley Park, Walton-on-Thames | Results |
| 21 May 2023 | First Round | Watford Town v Wokingham | Woodside, Watford | Results |
| 04 Jun 2023 | Second Round | Bexley v Brentwood | Manor Way, Bexley | Results |
| 11 Jun 2023 | Second Round | Blackheath v Shenfield | The Rectory Field, Blackheath | Results |
| 11 Jun 2023 | Second Round | East Molesey v Old Hamptonians | Memorial Cricket Ground, East Molesey | Results |
| 11 Jun 2023 | Second Round | Hornchurch v Buckhurst Hill | Harrow Lodge Park, Hornchurch | Results |
| 11 Jun 2023 | Second Round | Reigate Priory v South Hampstead | Park Lane, Reigate | Results |
| 11 Jun 2023 | Second Round | Roffey v Sutton | Crawley Road, Horsham | Results |
| 11 Jun 2023 | Second Round | Sandwich Town v Wanstead and Snaresbrook | The Butts, Sandwich | Results |
| 11 Jun 2023 | Second Round | Sawston and Babraham v Banstead | Spicer's Sports Ground, Sawston | Results |
| 11 Jun 2023 | Second Round | Spencer v Minster (Sheppey) | Spencer Cricket Club Ground, Earlsfield | Results |
| 11 Jun 2023 | Second Round | Waltham v Dartford | The Peter May Sports Centre, Walthamstow | Results |
| 11 Jun 2023 | Second Round | Walton-on-Thames v Ealing | Ashley Park, Walton-on-Thames | Results |
| 18 Jun 2023 | Second Round | Camberley v Harrow Town | Upper Verran Road, Camberley | Results |
| 25 Jun 2023 | Second Round | Harefield v Hornsey | Woods Cricket Ground, Harefield | Results |
| 25 Jun 2023 | Second Round | Totteridge Millhillians v Acton | Totteridge Green, Totteridge | Results |
| 25 Jun 2023 | Second Round | Watford Town v North Middlesex | Woodside, Watford | Results |
| 25 Jun 2023 | Second Round | Wimbledon v Finchley | Church Road, Wimbledon | Results |
| 02 Jul 2023 | Third Round | Brentwood v Reigate Priory | Old County Ground, Brentwood | Results |
| 02 Jul 2023 | Third Round | Hornchurch v East Molesey | Harrow Lodge Park, Hornchurch | Results |
| 09 Jul 2023 | Third Round | Acton v Walton-on-Thames | Manor Park Grounds, Acton | Results |
| 02 Jul 2023 | Third Round | Harrow Town v North Middlesex | Harrow Town Sports Club Ground, Harrow | Results |
| 02 Jul 2023 | Third Round | Hornsey v Sawston and Babraham | Tivoli Road, Hornsey | Results |
| 02 Jul 2023 | Third Round | Wimbledon v Spencer | Church Road, Wimbledon | Results |
| 16 Jul 2023 | Third Round | Roffey v Blackheath | Crawley Road, Horsham | Results |
| 02 Jul 2023 | Third Round | Sandwich Town v Waltham | The Butts, Sandwich | Results |
| 13 Aug 2023 | Quarter-Final | Hornchurch v Blackheath | Harrow Lodge Park, Hornchurch | Results |
| 23 Jul 2023 | Quarter-Final | Wimbledon v Sandwich Town | Church Road, Wimbledon | Results |
| 06 Aug 2023 | Quarter-Final | Walton-on-Thames v Brentwood | Ashley Park, Walton-on-Thames | Results |
| 13 Aug 2023 | Quarter-Final | Hornsey v Harrow Town | Tivoli Road, Hornsey | Results |
| 20 Aug 2023 | Semi-Final | Walton-on-Thames v Sandwich Town | not known | Results |
| 20 Aug 2023 | Semi-Final | Hornsey v Hornchurch | Tivoli Road, Hornsey | Results |
| 16 Sep 2023 | Final | Hornchurch v Walton-on-Thames | Upper Verran Road, Camberley | Results |
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