| 30 Apr 2008 | First Round | East Molesey v not known | not known | Results |
| 30 Apr 2008 | First Round | Hitchin v not known | not known | Results |
| 30 Apr 2008 | First Round | Ickenham v not known | not known | Results |
| 30 Apr 2008 | First Round | Saffron Walden v not known | not known | Results |
| 30 Apr 2008 | First Round | Shenfield v not known | not known | Results |
| 30 Apr 2008 | First Round | South Hampstead v not known | not known | Results |
| 30 Apr 2008 | First Round | South Woodford v not known | not known | Results |
| 30 Apr 2008 | First Round | Upminster v not known | not known | Results |
| 30 Apr 2008 | First Round | Waltham v not known | not known | Results |
| 05 May 2008 | First Round | Sidley v Cambridge Granta | Gullivers Sports Ground, Sidley | Results |
| 21 May 2008 | First Round | North Middlesex v Middlesex Tamils | North Middlesex Cricket Club Ground, Crouch End | Results |
| 22 May 2008 | First Round | Purley v Basingstoke and North Hants | The Ridge, Purley | Results |
| 23 May 2008 | First Round | Sutton v Old Wimbledonians | Cheam Road, Sutton | Results |
| 30 May 2008 | First Round | AJ Sports v Ford Sports Club | not known | Results |
| 30 May 2008 | First Round | Barbados Overseas Cricket Association v Egham | West Wickham Sports Club Ground, West Wickham | Results |
| 01 Jun 2008 | First Round | Aztecs v Bishop's Stortford | London Marathon Playing Fields, Barkingside | Results |
| 04 Jun 2008 | First Round | Ardleigh Green v North Mymms | Central Park, Harold Hill | Results |
| 06 Jun 2008 | Second Round | Hitchin v Saffron Walden | Lucas Lane, Hitchin | Results |
| 11 Jun 2008 | Second Round | Shenfield v East Molesey | Chelmsford Road, Shenfield | Results |
| 30 Jun 2008 | Second Round | Bishop's Stortford v Cambridge Granta | Cricketfield Lane, Bishop's Stortford | Results |
| 30 Jun 2008 | Second Round | Egham v Ardleigh Green | Vicarage Road, Egham | Results |
| 30 Jun 2008 | Second Round | Purley v AJ Sports | The Ridge, Purley | Results |
| 15 Jul 2008 | Second Round | South Woodford v Middlesex Tamils | Highfield Road, Woodford Green | Results |
| 16 Jul 2008 | Second Round | Ickenham v Waltham | Oak Avenue, Ickenham | Results |
| 04 Aug 2008 | Second Round | Upminster v South Hampstead | Upminster Park, Upminster | Results |
| 06 Aug 2008 | Quarter-Final | East Molesey v Saffron Walden | Memorial Cricket Ground, East Molesey | Results |
| 10 Aug 2008 | Quarter-Final | Purley v South Woodford | The Ridge, Purley | Results |
| 15 Aug 2008 | Quarter-Final | South Hampstead v Cambridge Granta | Milverton Road, Willesden | Results |
| 20 Aug 2008 | Quarter-Final | Ardleigh Green v Waltham | Central Park, Harold Hill | Results |
| 28 Aug 2008 | Semi-Final | East Molesey v Cambridge Granta | Memorial Cricket Ground, East Molesey | Results |
| 28 Aug 2008 | Semi-Final | South Woodford v Waltham | Highfield Road, Woodford Green | Results |
| 01 Sep 2008 | Final | Cambridge Granta v Waltham | Milverton Road, Willesden | Results |
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