| 11 May 2008 | First Round | Aztecs v Hutton | London Marathon Playing Fields, Barkingside | Results |
| 11 May 2008 | First Round | Bessborough v Brentwood | Headstone Recreation Ground, North Harrow | Results |
| 11 May 2008 | First Round | Bishop's Stortford v Chingford | Cricketfield Lane, Bishop's Stortford | Results |
| 11 May 2008 | First Round | Cockfosters v Colchester and East Essex | Chalk Lane, Cockfosters | Results |
| 11 May 2008 | First Round | Gidea Park and Romford v Hainault and Clayhall | Gidea Park Sports Ground, Romford | Results |
| 11 May 2008 | First Round | Gravesend v Hornchurch | Bat and Ball Ground, Gravesend | Results |
| 11 May 2008 | First Round | Harrow v Watford Town | Payne's Folly, Harrow | Results |
| 11 May 2008 | First Round | Hertford v Hampstead | Balls Park, Hertford | Results |
| 11 May 2008 | First Round | Hornsey v Ickenham | Tivoli Road, Hornsey | Results |
| 11 May 2008 | First Round | Knebworth Park v London Maccabi Vale | Knebworth Park, Knebworth | Results |
| 11 May 2008 | First Round | Old Emanuel v Mitcham | Metropolitan Police Sports Ground, Bushey | Results |
| 11 May 2008 | First Round | Potters Bar v Old Actonians | The Walk, Potters Bar | Results |
| 11 May 2008 | First Round | Radlett v Shenfield | Brunton Memorial Ground, Radlett | Results |
| 11 May 2008 | First Round | Sawbridgeworth v Shepherds Bush | Town Fields, Sawbridgeworth | Results |
| 11 May 2008 | First Round | South Woodford v Woodford Wells | Highfield Road, Woodford Green | Results |
| 25 May 2008 | First Round | Addiscombe v Beckenham | Sandilands, Croydon | Results |
| 25 May 2008 | First Round | Ashford v Beddington | Short Lane, Stanwell | Results |
| 25 May 2008 | First Round | Banstead v Bexley | Recreation Ground, Banstead | Results |
| 25 May 2008 | First Round | Bickley Park v East Molesey | Bickley Park Road, Bickley | Results |
| 25 May 2008 | First Round | Dartford v Esher | Hesketh Park, Dartford | Results |
| 25 May 2008 | First Round | Epsom v Three Bridges | Woodcote Road, Epsom | Results |
| 25 May 2008 | First Round | HSBC v Cheam | HSBC Sports and Social Club, Beckenham | Results |
| 25 May 2008 | First Round | Linden Park v Wokingham | Higher Common Ground, Tunbridge Wells | Results |
| 25 May 2008 | First Round | Metropolitan Police Bushey v Southgate | Metropolitan Police Sports Ground, Bushey | Results |
| 25 May 2008 | First Round | Orpington v Purley | Goddington Dene, Orpington | Results |
| 25 May 2008 | First Round | Welwyn Garden City v Enfield | Digswell Park, Welwyn Garden City | Results |
| 25 May 2008 | First Round | West Herts v Malden Wanderers | Park Avenue, Watford | Results |
| 01 Jun 2008 | First Round | Dulwich v Hayes | Turney Road, Dulwich | Results |
| 01 Jun 2008 | First Round | Ekco Monarchs and Trojans v Caribbean Anchor | Ekco Social and Sports Club Ground, Southend-on-Sea | Results |
| 01 Jun 2008 | First Round | Ilford v Wembley | Valentine's Park, Ilford | Results |
| 01 Jun 2008 | First Round | Richmond v Wimbledon | Old Deer Park, Richmond | Results |
| 01 Jun 2008 | First Round | South Hampstead v Uxbridge | Milverton Road, Willesden | Results |
| 15 Jun 2008 | Second Round | Ardleigh Green v Welwyn Garden City | Central Park, Harold Hill | Results |
| 15 Jun 2008 | Second Round | Basingstoke and North Hants v Malden Wanderers | May's Bounty, Basingstoke | Results |
| 15 Jun 2008 | Second Round | Beaconsfield v Hertford | Wilton Park, Beaconsfield | Results |
| 15 Jun 2008 | Second Round | Blackheath v Potters Bar | The Rectory Field, Blackheath | Results |
| 15 Jun 2008 | Second Round | Brentham v Dartford | Brentham Sports Club Ground, Ealing | Results |
| 15 Jun 2008 | Second Round | Bromley v Linden Park | Plaistow Lane, Bromley | Results |
| 15 Jun 2008 | Second Round | Brondesbury v Aztecs | Harman Drive, Brondesbury | Results |
| 15 Jun 2008 | Second Round | BWIA Cavaliers v Cheam | North Middlesex Cricket Club Ground, Crouch End | Results |
| 15 Jun 2008 | Second Round | Ealing v Hayes | Corfton Road, Ealing | Results |
| 15 Jun 2008 | Second Round | Eastcote v Bishop's Stortford | Haydon Hall, Eastcote | Results |
| 15 Jun 2008 | Second Round | Finchley v East Molesey | Arden Field, Finchley | Results |
| 15 Jun 2008 | Second Round | Fives and Heronians v Harrow | The Paddock, Chigwell | Results |
| 15 Jun 2008 | Second Round | High Wycombe v Wembley | London Road, High Wycombe | Results |
| 15 Jun 2008 | Second Round | Lordswood v Hainault and Clayhall | Martin Grove, Lordswood | Results |
| 15 Jun 2008 | Second Round | Old Mid-Whitgiftian v Hornsey | Old Mid-Whitgiftian Association Ground, Sanderstead | Results |
| 15 Jun 2008 | Second Round | Osterley v Colchester and East Essex | Tentelow Lane, Osterley | Results |
| 15 Jun 2008 | Second Round | Oxford v Sawbridgeworth | Rover Cowley Sports and Social Club Ground, Cowley | Results |
| 15 Jun 2008 | Second Round | Reigate Priory v Gravesend | Park Lane, Reigate | Results |
| 15 Jun 2008 | Second Round | Saffron Walden v Knebworth Park | Anglo-American Playing Fields, Saffron Walden | Results |
| 15 Jun 2008 | Second Round | Spencer v South Hampstead | Spencer Cricket Club Ground, Earlsfield | Results |
| 15 Jun 2008 | Second Round | St Margaretsbury v Mitcham | The Receation Ground, Stanstead Abbotts | Results |
| 15 Jun 2008 | Second Round | Stanmore v Woodford Wells | Stanmore Common, Stanmore | Results |
| 15 Jun 2008 | Second Round | Sunbury v Ekco Monarchs and Trojans | Kenton Court Meadow, Sunbury-on-Thames | Results |
| 15 Jun 2008 | Second Round | Sutton v Three Bridges | Cheam Road, Sutton | Results |
| 15 Jun 2008 | Second Round | Teddington v Brentwood | Teddington Cricket Club Ground, Bushy Park, Teddington | Results |
| 15 Jun 2008 | Second Round | Tring Park v Radlett | London Road, Tring | Results |
| 15 Jun 2008 | Second Round | Upminster v Bexley | Upminster Park, Upminster | Results |
| 15 Jun 2008 | Second Round | Waltham v Metropolitan Police Bushey | The Peter May Sports Centre, Walthamstow | Results |
| 15 Jun 2008 | Second Round | Walton-on-Thames v Beddington | Ashley Park, Walton-on-Thames | Results |
| 15 Jun 2008 | Second Round | Wanstead v Beckenham | Overton Drive, Wanstead | Results |
| 15 Jun 2008 | Second Round | Weybridge v Wimbledon | The Cricket Green, Weybridge | Results |
| 15 Jun 2008 | Second Round | Winchmore Hill v Orpington | The Paulin Ground, Winchmore Hill | Results |
| 29 Jun 2008 | Third Round | Ardleigh Green v Sutton | Central Park, Harold Hill | Results |
| 29 Jun 2008 | Third Round | Beaconsfield v St Margaretsbury | Wilton Park, Beaconsfield | Results |
| 29 Jun 2008 | Third Round | Bishop's Stortford v Beddington | Cricketfield Lane, Bishop's Stortford | Results |
| 29 Jun 2008 | Third Round | Bromley v Wanstead | Plaistow Lane, Bromley | Results |
| 29 Jun 2008 | Third Round | Brondesbury v Reigate Priory | Harman Drive, Brondesbury | Results |
| 29 Jun 2008 | Third Round | BWIA Cavaliers v Radlett | North Middlesex Cricket Club Ground, Crouch End | Results |
| 29 Jun 2008 | Third Round | Ealing v Dartford | Corfton Road, Ealing | Results |
| 29 Jun 2008 | Third Round | High Wycombe v Woodford Wells | London Road, High Wycombe | Results |
| 29 Jun 2008 | Third Round | Old Mid-Whitgiftian v Finchley | Old Mid-Whitgiftian Association Ground, Sanderstead | Results |
| 29 Jun 2008 | Third Round | Orpington v Osterley | Goddington Dene, Orpington | Results |
| 29 Jun 2008 | Third Round | Oxford v Malden Wanderers | Rover Cowley Sports and Social Club Ground, Cowley | Results |
| 29 Jun 2008 | Third Round | Potters Bar v Saffron Walden | The Walk, Potters Bar | Results |
| 29 Jun 2008 | Third Round | South Hampstead v Hainault and Clayhall | Milverton Road, Willesden | Results |
| 29 Jun 2008 | Third Round | Sunbury v Waltham | Kenton Court Meadow, Sunbury-on-Thames | Results |
| 29 Jun 2008 | Third Round | Teddington v Fives and Heronians | Teddington Cricket Club Ground, Bushy Park, Teddington | Results |
| 29 Jun 2008 | Third Round | Upminster v Wimbledon | Upminster Park, Upminster | Results |
| 13 Jul 2008 | Fourth Round | Ardleigh Green v St Margaretsbury | Central Park, Harold Hill | Results |
| 13 Jul 2008 | Fourth Round | Bishop's Stortford v Finchley | Cricketfield Lane, Bishop's Stortford | Results |
| 13 Jul 2008 | Fourth Round | Brondesbury v Ealing | Harman Drive, Brondesbury | Results |
| 13 Jul 2008 | Fourth Round | Osterley v South Hampstead | Tentelow Lane, Osterley | Results |
| 27 Jul 2008 | Fourth Round | Potters Bar v High Wycombe | The Walk, Potters Bar | Results |
| 13 Jul 2008 | Fourth Round | Radlett v Sunbury | Brunton Memorial Ground, Radlett | Results |
| 13 Jul 2008 | Fourth Round | Teddington v Bromley | Teddington Cricket Club Ground, Bushy Park, Teddington | Results |
| 13 Jul 2008 | Fourth Round | Wimbledon v Malden Wanderers | Church Road, Wimbledon | Results |
| 27 Jul 2008 | Quarter-Final | Bishop's Stortford v Ardleigh Green | Cricketfield Lane, Bishop's Stortford | Results |
| 27 Jul 2008 | Quarter-Final | Bromley v Ealing | Plaistow Lane, Bromley | Results |
| 27 Jul 2008 | Quarter-Final | Osterley v Wimbledon | Tentelow Lane, Osterley | Results |
| 03 Aug 2008 | Quarter-Final | Sunbury v Potters Bar | Kenton Court Meadow, Sunbury-on-Thames | Results |
| 17 Aug 2008 | Semi-Final | Ealing v Bishop's Stortford | Corfton Road, Ealing | Results |
| 17 Aug 2008 | Semi-Final | Sunbury v Wimbledon | Kenton Court Meadow, Sunbury-on-Thames | Results |
| 14 Sep 2008 | Final | Ealing v Sunbury | Corfton Road, Ealing | Results |
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