| 25 Apr 2009 | First Round | Woodmansterne v Ripley | Carshalton Road, Woodmansterne | Results |
| 25 Apr 2009 | First Round | Guildford City v Old Tenisonians | Stoke Park, Guildford | Results |
| 25 Apr 2009 | First Round | Sanderstead v Effingham | The Old Saw Mill, Sanderstead | Results |
| 02 May 2009 | Second Round | Merrow v Ripley | Epsom Road, Merrow | Results |
| 02 May 2009 | Second Round | Deando Ruxley v Long Ditton | Ruxley Lane, Ewell | Results |
| 02 May 2009 | Second Round | Frimley v Old Pauline | Chobham Road, Frimley | Results |
| 02 May 2009 | Second Round | Shepperton v Battersea Ironsides | Manor Park, Shepperton | Results |
| 02 May 2009 | Second Round | Caterham v Whiteley Village | Park Avenue, Caterham | Results |
| 02 May 2009 | Second Round | Horley v Old Suttonians | Horley Row, Horley | Results |
| 02 May 2009 | Second Round | Wandgas v Oxted and Limpsfield | Grafton Road, Worcester Park | Results |
| 02 May 2009 | Second Round | Westfield Saints v West End Esher | Westfield District Cricket and Sports Club Ground, Woking | Results |
| 02 May 2009 | Second Round | Carshalton v Roehampton | Telegraph Road, Putney | Results |
| 02 May 2009 | Second Round | Merstham v Byfleet Saturday | Quality Street, Merstham | Results |
| 02 May 2009 | Second Round | Hampton Wick Royal v Kempton | Bushy Park, Hampton Wick | Results |
| 02 May 2009 | Second Round | Godalming v Haslemere | Holloway Hill Recreation Ground, Godalming | Results |
| 02 May 2009 | Second Round | Old Tiffinians v Lingfield | Grist Memorial Ground, East Molesey | Results |
| 02 May 2009 | Second Round | Worplesdon and Burpham v Ewhurst | The Memorial Field, Worplesdon | Results |
| 02 May 2009 | Second Round | Weybridge Vandals v Chobham | Brown Acres, Walton-on-Thames | Results |
| 02 May 2009 | Second Round | Guildford City v Sanderstead | Stoke Park, Guildford | Results |
| 25 May 2009 | Third Round | Oxted and Limpsfield v Westfield Saints | Master Park, Oxted | Results |
| 25 May 2009 | Third Round | Lingfield v Worplesdon and Burpham | Godstone Road, Lingfield | Results |
| 25 May 2009 | Third Round | Chobham v Guildford City | High Street, Chobham | Results |
| 25 May 2009 | Third Round | Deando Ruxley v Ripley | Ruxley Lane, Ewell | Results |
| 25 May 2009 | Third Round | Frimley v Battersea Ironsides | Chobham Road, Frimley | Results |
| 25 May 2009 | Third Round | Caterham v Horley | Park Avenue, Caterham | Results |
| 25 May 2009 | Third Round | Roehampton v Byfleet Saturday | Telegraph Road, Putney | Results |
| 31 May 2009 | Third Round | Godalming v Kempton | Holloway Hill Recreation Ground, Godalming | Results |
| 28 Jun 2009 | Quarter-Final | Deando Ruxley v Frimley | Ruxley Lane, Ewell | Results |
| 28 Jun 2009 | Quarter-Final | Caterham v Oxted and Limpsfield | Park Avenue, Caterham | Results |
| 28 Jun 2009 | Quarter-Final | Byfleet Saturday v Kempton | Parvis Road, Byfleet | Results |
| 12 Jul 2009 | Quarter-Final | Lingfield v Chobham | Godstone Road, Lingfield | Results |
| 02 Aug 2009 | Semi-Final | Frimley v Oxted and Limpsfield | Chobham Road, Frimley | Results |
| 02 Aug 2009 | Semi-Final | Byfleet Saturday v Lingfield | Parvis Road, Byfleet | Results |
| 06 Sep 2009 | Final | Oxted and Limpsfield v Lingfield | Holloway Hill Recreation Ground, Godalming | Results |
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