| 09 May 2021 | First Round | Harefield v Wanstead and Snaresbrook | Woods Cricket Ground, Harefield | Results |
| 23 May 2021 | First Round | Camberley v Watford Town | Upper Verran Road, Camberley | Results |
| 23 May 2021 | First Round | Enfield v Blackheath | Lincoln Road, Enfield | Results |
| 23 May 2021 | First Round | Hoddesdon v Bishop's Stortford | Lowfield, Hoddesdon | Results |
| 23 May 2021 | First Round | Hutton v Minster (Sheppey) | The Polo Field Ground, Hutton | Results |
| 23 May 2021 | First Round | Ickenham v Banstead | Oak Avenue, Ickenham | Results |
| 23 May 2021 | First Round | Oxted and Limpsfield v Christchurch | Master Park, Oxted | Results |
| 23 May 2021 | First Round | Shenfield v Bromley | Chelmsford Road, Shenfield | Results |
| 23 May 2021 | First Round | Three Bridges v Old Wimbledonians | Three Bridges Road, Three Bridges | Results |
| 23 May 2021 | First Round | Tunbridge Wells v Sutton | The Nevill Ground, Tunbridge Wells | Results |
| 30 May 2021 | First Round | Braywood v Aldershot | The Turnbull Cricket Ground, Fifield | Results |
| 31 May 2021 | First Round | Indian Gymkhana v Upminster | Thornbury Avenue, Osterley | Results |
| 06 Jun 2021 | First Round | Totteridge Millhillians v Waltham | Totteridge Green, Totteridge | Results |
| 08 Jun 2021 | First Round | Eastcote v Old Hamptonians | Haydon Hall, Eastcote | Results |
| 13 Jun 2021 | Second Round | Alexandra Park v Watford Town | The Racecourse Ground, Alexandra Park | Results |
| 13 Jun 2021 | Second Round | Bexley v Minster (Sheppey) | Manor Way, Bexley | Results |
| 13 Jun 2021 | Second Round | Bromley v Oxted and Limpsfield | Plaistow Lane, Bromley | Results |
| 13 Jun 2021 | First Round | Broxbourne v Finchley | Broxbourne Sports Club Ground, Broxbourne | Results |
| 13 Jun 2021 | Second Round | Cambridge v Enfield | Caldecote Recreation Ground, Caldecote | Results |
| 13 Jun 2021 | Second Round | Crouch End v East Molesey | The Calthorpe Ground, Crouch End | Results |
| 13 Jun 2021 | Second Round | Hornchurch v Sutton | Harrow Lodge Park, Hornchurch | Results |
| 13 Jun 2021 | Second Round | Ickenham v Aldershot | Oak Avenue, Ickenham | Results |
| 13 Jun 2021 | Second Round | Sandwich Town v Brentwood | The Butts, Sandwich | Results |
| 13 Jun 2021 | First Round | South Hampstead v Sawston and Babraham | Milverton Road, Willesden | Results |
| 13 Jun 2021 | Second Round | Upminster v Reigate Priory | Upminster Park, Upminster | Results |
| 13 Jun 2021 | Second Round | Walton-on-Thames v Waltham | Ashley Park, Walton-on-Thames | Results |
| 13 Jun 2021 | Second Round | Wimbledon v Hoddesdon | Church Road, Wimbledon | Results |
| 20 Jun 2021 | Second Round | Three Bridges v Orsett and Thurrock | Three Bridges Road, Three Bridges | Results |
| 27 Jun 2021 | Second Round | Harefield v Acton | Woods Cricket Ground, Harefield | Results |
| 27 Jun 2021 | Second Round | Stanmore v Finchley | Stanmore Common, Stanmore | Results |
| 27 Jun 2021 | Second Round | Sunbury v Eastcote | Kenton Court Meadow, Sunbury-on-Thames | Results |
| 04 Jul 2021 | Third Round | Bexley v Sunbury | Manor Way, Bexley | Results |
| 08 Aug 2021 | Third Round | Hoddesdon v Stanmore | Lowfield, Hoddesdon | Results |
| 11 Jul 2021 | Third Round | Hornchurch v Sandwich Town | Harrow Lodge Park, Hornchurch | Results |
| 04 Jul 2021 | Third Round | Three Bridges v Harefield | Three Bridges Road, Three Bridges | Results |
| 04 Jul 2021 | Third Round | Oxted and Limpsfield v Reigate Priory | Master Park, Oxted | Results |
| 04 Jul 2021 | Second Round | Sawston and Babraham v Ealing | Spicer's Sports Ground, Sawston | Results |
| 04 Jul 2021 | Third Round | Walton-on-Thames v Enfield | Ashley Park, Walton-on-Thames | Results |
| 18 Jul 2021 | Third Round | Watford Town v Ickenham | Woodside, Watford | Results |
| 25 Jul 2021 | Third Round | Sawston and Babraham v East Molesey | Spicer's Sports Ground, Sawston | Results |
| 25 Jul 2021 | Quarter-Final | Bexley v Ickenham | Manor Way, Bexley | Results |
| 25 Jul 2021 | Quarter-Final | Sandwich Town v Walton-on-Thames | The Butts, Sandwich | Results |
| 25 Jul 2021 | Quarter-Final | Reigate Priory v Three Bridges | Park Lane, Reigate | Results |
| 15 Aug 2021 | Quarter-Final | East Molesey v Hoddesdon | Memorial Cricket Ground, East Molesey | Results |
| 15 Aug 2021 | Semi-Final | Reigate Priory v Sandwich Town | Park Lane, Reigate | Results |
| 22 Aug 2021 | Semi-Final | East Molesey v Bexley | Memorial Cricket Ground, East Molesey | Results |
| 18 Sep 2021 | Final | East Molesey v Sandwich Town | Old County Ground, Brentwood | Results |
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