| 10 May 2009 | First Round | Beaconsfield v Stanmore | Wilton Park, Beaconsfield | Results |
| 10 May 2009 | First Round | Bexley v John Fisher | Manor Way, Bexley | Results |
| 10 May 2009 | First Round | Bromley v Tunbridge Wells | Plaistow Lane, Bromley | Results |
| 10 May 2009 | First Round | Buckhurst Hill v Hadleigh and Thundersley | Roding Lane, Buckhurst Hill | Results |
| 10 May 2009 | First Round | Chingford v Ardleigh Green | Forest Side, Chingford | Results |
| 10 May 2009 | First Round | Ealing v Walton-on-Thames | Corfton Road, Ealing | Results |
| 10 May 2009 | First Round | Fives and Heronians v Asian | The Paddock, Chigwell | Results |
| 10 May 2009 | First Round | Gidea Park and Romford v Saffron Walden | Gidea Park Sports Ground, Romford | Results |
| 10 May 2009 | First Round | Gore Court v Blackheath | The Grove, Sittingbourne | Results |
| 10 May 2009 | First Round | Harold Wood v Hornchurch | Harold Wood Park, Harold Wood | Results |
| 10 May 2009 | First Round | Harrow v Winchmore Hill | Payne's Folly, Harrow | Results |
| 10 May 2009 | First Round | Harrow Town v London Maccabi Vale | Harrow Town Sports Club Ground, Harrow | Results |
| 10 May 2009 | First Round | HSBC v Purley | HSBC Sports and Social Club, Beckenham | Results |
| 10 May 2009 | First Round | Lordswood v Bickley Park | Martin Grove, Lordswood | Results |
| 10 May 2009 | First Round | Malden Wanderers v Egham | Cambridge Avenue, New Malden | Results |
| 10 May 2009 | First Round | Oxford v Brondesbury | Rover Cowley Sports and Social Club Ground, Cowley | Results |
| 10 May 2009 | First Round | Royal Ascot v Normandy | Ascot Heath, Ascot | Results |
| 10 May 2009 | First Round | Sawbridgeworth v Waltham | Town Fields, Sawbridgeworth | Results |
| 10 May 2009 | First Round | Shenfield v Bishop's Stortford | Chelmsford Road, Shenfield | Results |
| 10 May 2009 | First Round | Shipton-under-Wychwood v Radlett | Burford Road, Shipton-under-Wychwood | Results |
| 10 May 2009 | First Round | Slough v Brentham | Upton Court Road, Slough | Results |
| 10 May 2009 | First Round | South Hampstead v Wembley | Milverton Road, Willesden | Results |
| 10 May 2009 | First Round | Teddington v Valley End | Teddington Cricket Club Ground, Bushy Park, Teddington | Results |
| 10 May 2009 | First Round | Upminster v Orpington | Upminster Park, Upminster | Results |
| 10 May 2009 | First Round | Walthamstow v Hainault and Clayhall | Buck Walk, Walthamstow | Results |
| 10 May 2009 | First Round | Wanstead v Ekco Monarchs and Trojans | Overton Drive, Wanstead | Results |
| 10 May 2009 | First Round | Windsor v Shepherds Bush | Home Park, Windsor | Results |
| 10 May 2009 | First Round | Wycombe House v Sunbury | Jersey Road, Osterley | Results |
| 17 May 2009 | First Round | East Molesey v Richmond | Memorial Cricket Ground, East Molesey | Results |
| 17 May 2009 | First Round | Hampstead v Finchley | Lymington Road, Hampstead | Results |
| 17 May 2009 | First Round | High Wycombe v Southgate | London Road, High Wycombe | Results |
| 14 Jun 2009 | Second Round | Blackheath v Ardleigh Green | The Rectory Field, Blackheath | Results |
| 18 Jun 2009 | Second Round | Fives and Heronians v Stanmore | The Paddock, Chigwell | Results |
| 07 Jun 2009 | Second Round | HSBC v Waltham | HSBC Sports and Social Club, Beckenham | Results |
| 07 Jun 2009 | Second Round | Radlett v Bromley | Brunton Memorial Ground, Radlett | Results |
| 14 Jun 2009 | Second Round | Shepherds Bush v Bexley | The New Ground, Shepherds Bush | Results |
| 07 Jun 2009 | Second Round | Valley End v East Molesey | Windlesham Road, Valley End | Results |
| 07 Jun 2009 | Second Round | Winchmore Hill v Sunbury | The Paulin Ground, Winchmore Hill | Results |
| 15 Jun 2009 | Second Round | Ealing v Oxford | Corfton Road, Ealing | Results |
| 07 Jun 2009 | Second Round | Hayes v Finchley | Barnet Wood Road, Hayes | Results |
| 07 Jun 2009 | Second Round | Normandy v Harold Wood | Hunts Hill Road, Normandy | Results |
| 07 Jun 2009 | Second Round | Shenfield v Bickley Park | Chelmsford Road, Shenfield | Results |
| 07 Jun 2009 | Second Round | Upminster v Wanstead | Upminster Park, Upminster | Results |
| 07 Jun 2009 | Second Round | Walthamstow v High Wycombe | Buck Walk, Walthamstow | Results |
| 07 Jun 2009 | Second Round | Brentham v Harrow Town | Brentham Sports Club Ground, Ealing | Results |
| 14 Jun 2009 | Second Round | Gidea Park and Romford v South Hampstead | Gidea Park Sports Ground, Romford | Results |
| 07 Jun 2009 | Second Round | Malden Wanderers v Hadleigh and Thundersley | Cambridge Avenue, New Malden | Results |
| 21 Jun 2009 | Third Round | East Molesey v Bromley | Memorial Cricket Ground, East Molesey | Results |
| 21 Jun 2009 | Third Round | Blackheath v High Wycombe | The Rectory Field, Blackheath | Results |
| 21 Jun 2009 | Third Round | Sunbury v Malden Wanderers | Kenton Court Meadow, Sunbury-on-Thames | Results |
| 21 Jun 2009 | Third Round | Bexley v Bickley Park | Manor Way, Bexley | Results |
| 21 Jun 2009 | Third Round | Harold Wood v Waltham | Harold Wood Park, Harold Wood | Results |
| 21 Jun 2009 | Third Round | Fives and Heronians v Wanstead | The Paddock, Chigwell | Results |
| 21 Jun 2009 | Third Round | Finchley v Gidea Park and Romford | Arden Field, Finchley | Results |
| 21 Jun 2009 | Third Round | Oxford v Harrow Town | Rover Cowley Sports and Social Club Ground, Cowley | Results |
| 05 Jul 2009 | Quarter-Final | Blackheath v Oxford | The Rectory Field, Blackheath | Results |
| 05 Jul 2009 | Quarter-Final | Bexley v Waltham | Manor Way, Bexley | Results |
| 05 Jul 2009 | Quarter-Final | Sunbury v Wanstead | Kenton Court Meadow, Sunbury-on-Thames | Results |
| 19 Jul 2009 | Quarter-Final | East Molesey v Finchley | Memorial Cricket Ground, East Molesey | Results |
| 26 Jul 2009 | Semi-Final | Blackheath v Waltham | The Rectory Field, Blackheath | Results |
| 26 Jul 2009 | Semi-Final | Finchley v Sunbury | Arden Field, Finchley | Results |
| 09 Aug 2009 | Final | Finchley v Waltham | Shenley Sports Ground, Shenley | Results |
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