| 26 Apr 2008 | First Round | Shepperton v West End Esher | Manor Park, Shepperton | Results |
| 26 Apr 2008 | First Round | Old Tenisonians v Old Tiffinians | London University Ground, Motspur Park | Results |
| 26 Apr 2008 | First Round | Lingfield v Stoke D'Abernon | Godstone Road, Lingfield | Results |
| 26 Apr 2008 | First Round | Wandgas v Carshalton | Grafton Road, Worcester Park | Results |
| 03 May 2008 | Second Round | Horley v Kempton | Horley Row, Horley | Results |
| 03 May 2008 | Second Round | Ewhurst v Whiteley Village | Ewhurst Green, Ewhurst | Results |
| 03 May 2008 | Second Round | Caterham v Southbank | Park Avenue, Caterham | Results |
| 03 May 2008 | Second Round | Stoke D'Abernon v Wandgas | Stoke D'Abernon Recreation Ground, Stoke D'Abernon | Results |
| 03 May 2008 | Second Round | Byfleet Saturday v Merrow | Parvis Road, Byfleet | Results |
| 03 May 2008 | Second Round | Battersea Ironsides v Worplesdon and Burpham | Burntwood Lane, Earlsfield | Results |
| 03 May 2008 | Second Round | Woodmansterne v Weybridge Vandals | Carshalton Road, Woodmansterne | Results |
| 03 May 2008 | Second Round | Effingham v Ripley | Effingham Common, Effingham | Results |
| 03 May 2008 | Second Round | Haslemere v Deando Ruxley | Haslemere Recreation Ground, Haslemere | Results |
| 03 May 2008 | Second Round | Old Tiffinians v West End Esher | Grist Memorial Ground, East Molesey | Results |
| 03 May 2008 | Second Round | Sanderstead v Guildford City | The Old Saw Mill, Sanderstead | Results |
| 03 May 2008 | Second Round | Addiscombe v Old Suttonians | Sandilands, Croydon | Results |
| 03 May 2008 | Second Round | Old Pauline v Roehampton | Colets, Thames Ditton | Results |
| 03 May 2008 | Second Round | Hampton Wick Royal v Godalming | Bushy Park, Hampton Wick | Results |
| 11 May 2008 | Second Round | Westfield Saints v Merstham | Westfield District Cricket and Sports Club Ground, Woking | Results |
| 18 May 2008 | Second Round | Long Ditton v Frimley | Stokes Field, Long Ditton | Results |
| 26 May 2008 | Third Round | Battersea Ironsides v Weybridge Vandals | Burntwood Lane, Earlsfield | Results |
| 26 May 2008 | Third Round | Southbank v Stoke D'Abernon | Turney Road, Dulwich | Results |
| 26 May 2008 | Third Round | Long Ditton v Whiteley Village | Stokes Field, Long Ditton | Results |
| 08 Jun 2008 | Third Round | Effingham v Deando Ruxley | Effingham Common, Effingham | Results |
| 15 Jun 2008 | Third Round | Godalming v Byfleet Saturday | Holloway Hill Recreation Ground, Godalming | Results |
| 15 Jun 2008 | Third Round | Addiscombe v Old Pauline | Sandilands, Croydon | Results |
| 22 Jun 2008 | Third Round | Westfield Saints v Horley | Westfield District Cricket and Sports Club Ground, Woking | Results |
| 29 Jun 2008 | Quarter-Final | Horley v Godalming | Horley Row, Horley | Results |
| 29 Jun 2008 | Quarter-Final | Whiteley Village v Stoke D'Abernon | Coombe Lane, Whiteley Village | Results |
| 29 Jun 2008 | Quarter-Final | Battersea Ironsides v Effingham | Burntwood Lane, Earlsfield | Results |
| 29 Jun 2008 | Third Round | Old Tiffinians v Sanderstead | Grist Memorial Ground, East Molesey | Results |
| 13 Jul 2008 | Quarter-Final | Old Tiffinians v Addiscombe | Grist Memorial Ground, East Molesey | Results |
| 27 Jul 2008 | Semi-Final | Addiscombe v Godalming | Sandilands, Croydon | Results |
| 27 Jul 2008 | Semi-Final | Effingham v Whiteley Village | Effingham Common, Effingham | Results |
| 07 Sep 2008 | Final | Addiscombe v Whiteley Village | Sandilands, Croydon | Results |
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