| 25 May 2009 | First Round | Sawbridgeworth v Bishop's Stortford | Town Fields, Sawbridgeworth | Results |
| 25 May 2009 | First Round | Letchworth v Potters Bar | Whitehorn Lane, Letchworth | Results |
| 26 May 2009 | First Round | Cumnor v Oxford | Cumnor Cricket Club Ground, Cumnor | Results |
| 27 May 2009 | First Round | Harefield v Gerrards Cross | Woods Cricket Ground, Harefield | Results |
| 27 May 2009 | First Round | Harpenden v St Albans | The Common, Harpenden | Results |
| 27 May 2009 | First Round | West Herts v Radlett | Park Avenue, Watford | Results |
| 27 May 2009 | First Round | Reading v Henley | Sonning Lane, Reading | Results |
| 27 May 2009 | First Round | Finchampstead v Wokingham | Finchampstead Park, Finchampstead | Results |
| 27 May 2009 | First Round | Thatcham Town v Maidenhead and Bray | Browns Sports Field, Thatcham | Results |
| 27 May 2009 | First Round | Banbury v Bicester and North Oxford | White Post Road, Bodicote | Results |
| 27 May 2009 | First Round | Welwyn Garden City v Knebworth Park | Digswell Park, Welwyn Garden City | Results |
| 27 May 2009 | First Round | Stevenage v Hitchin | Ditchmore Lane, Stevenage | Results |
| 27 May 2009 | First Round | Aston Rowant v Tring Park | The Butts Way, Kingston Blount | Results |
| 03 Jun 2009 | First Round | Amersham v High Wycombe | Shardeloes, Amersham | Results |
| 25 Jun 2009 | First Round | Kew v Slough | Kew Green, Kew | Results |
| 04 Jun 2009 | First Round | Beaconsfield v Burnham | Wilton Park, Beaconsfield | Results |
| 24 Jun 2009 | Second Round | Hitchin v Letchworth | Lucas Lane, Hitchin | Results |
| 24 Jun 2009 | Second Round | Welwyn Garden City v Bishop's Stortford | Digswell Park, Welwyn Garden City | Results |
| 24 Jun 2009 | Second Round | Aston Rowant v Oxford | The Butts Way, Kingston Blount | Results |
| 01 Jul 2009 | Second Round | Banbury v Burnham | White Post Road, Bodicote | Results |
| 16 Jun 2009 | Second Round | Harpenden v West Herts | The Common, Harpenden | Results |
| 01 Jul 2009 | Second Round | Henley v Finchampstead | The Brakspear Ground, Remenham | Results |
| 24 Jun 2009 | Second Round | High Wycombe v Gerrards Cross | London Road, High Wycombe | Results |
| 16 Jul 2009 | Second Round | Thatcham Town v Slough | Browns Sports Field, Thatcham | Results |
| 22 Jul 2009 | Quarter-Final | Welwyn Garden City v Letchworth | Digswell Park, Welwyn Garden City | Results |
| 30 Jul 2009 | Quarter-Final | Banbury v Oxford | White Post Road, Bodicote | Results |
| 22 Jul 2009 | Quarter-Final | Gerrards Cross v West Herts | Dukes Lane, Gerrards Cross | Results |
| 22 Jul 2009 | Quarter-Final | Henley v Slough | The Brakspear Ground, Remenham | Results |
| 07 Aug 2009 | Semi-Final | Henley v Banbury | The Brakspear Ground, Remenham | Results |
| 07 Aug 2009 | Semi-Final | Welwyn Garden City v Gerrards Cross | Digswell Park, Welwyn Garden City | Results |
| 09 Aug 2009 | Final | Welwyn Garden City v Henley | Digswell Park, Welwyn Garden City | Results |
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