| 25 May 2014 | First Round | Acton v Old Rutlishians | Manor Park Grounds, Acton | Results |
| 25 May 2014 | First Round | Amersham v Ickenham | Shardeloes, Amersham | Results |
| 25 May 2014 | First Round | Beaconsfield v Ealing | Wilton Park, Beaconsfield | Results |
| 25 May 2014 | First Round | Beddington v HSBC | Beddington Park, Wallington | Results |
| 25 May 2014 | First Round | Bromley v Enfield | Plaistow Lane, Bromley | Results |
| 25 May 2014 | First Round | Buckhurst Hill v Bexley | Roding Lane, Buckhurst Hill | Results |
| 25 May 2014 | First Round | Burnham v Reigate Priory | The Memorial Ground, Burnham | Results |
| 25 May 2014 | First Round | Catford and Cyphers v Dartford | Rubens Street Oval, Catford | Results |
| 25 May 2014 | First Round | Chingford v Aston Rowant | Forest Side, Chingford | Results |
| 25 May 2014 | First Round | Cockfosters v Sanderstead | Chalk Lane, Cockfosters | Results |
| 25 May 2014 | First Round | Colchester and East Essex v Hornchurch | Castle Park Cricket Ground, Colchester | Results |
| 25 May 2014 | First Round | Fives and Heronians v Tunbridge Wells | The Paddock, Chigwell | Results |
| 25 May 2014 | First Round | Hadleigh and Thundersley v Harlow Town | John H Burrows Recreation Ground, Hadleigh | Results |
| 25 May 2014 | First Round | Harold Wood v Gidea Park and Romford | Harold Wood Park, Harold Wood | Results |
| 25 May 2014 | First Round | Hertford v Harpenden | Balls Park, Hertford | Results |
| 25 May 2014 | First Round | Kempton v East Molesey | The Kempton Ground, Sunbury-on-Thames | Results |
| 25 May 2014 | First Round | Lordswood v Hayes | Martin Grove, Lordswood | Results |
| 25 May 2014 | First Round | North Maidenhead v Brentham | Summerleaze Road, Maidenhead | Results |
| 25 May 2014 | First Round | Richmond v Chesham | Old Deer Park, Richmond | Results |
| 25 May 2014 | First Round | Sandwich Town v Orpington | The Butts, Sandwich | Results |
| 25 May 2014 | First Round | Sawbridgeworth v Bickley Park | Town Fields, Sawbridgeworth | Results |
| 25 May 2014 | First Round | Shenfield v Hampstead | Chelmsford Road, Shenfield | Results |
| 25 May 2014 | First Round | South Hampstead v Stanmore | Milverton Road, Willesden | Results |
| 25 May 2014 | First Round | Teddington v Walton-on-Thames | Teddington Cricket Club Ground, Bushy Park, Teddington | Results |
| 25 May 2014 | First Round | Upminster v John Fisher | Upminster Park, Upminster | Results |
| 25 May 2014 | First Round | Valley End v Oxford | Windlesham Road, Valley End | Results |
| 25 May 2014 | First Round | Wanstead v Godalming | Overton Drive, Wanstead | Results |
| 25 May 2014 | First Round | Weybridge v Watford Town | The Cricket Green, Weybridge | Results |
| 15 Jun 2014 | Second Round | Lordswood v Sunbury | Martin Grove, Lordswood | Results |
| 15 Jun 2014 | Second Round | Bexley v Sandwich Town | Manor Way, Bexley | Results |
| 15 Jun 2014 | Second Round | Ickenham v Reigate Priory | Oak Avenue, Ickenham | Results |
| 15 Jun 2014 | Second Round | Colchester and East Essex v Shenfield | Castle Park Cricket Ground, Colchester | Results |
| 15 Jun 2014 | Second Round | Waltham v HSBC | The Peter May Sports Centre, Walthamstow | Results |
| 15 Jun 2014 | Second Round | Catford and Cyphers v Richmond | Rubens Street Oval, Catford | Results |
| 15 Jun 2014 | Second Round | Brentham v Harold Wood | Brentham Sports Club Ground, Ealing | Results |
| 15 Jun 2014 | Second Round | Walton-on-Thames v Brentwood | Ashley Park, Walton-on-Thames | Results |
| 15 Jun 2014 | Second Round | Harlow Town v Stanmore | Ash Tree Fields, Harlow | Results |
| 15 Jun 2014 | Second Round | Weybridge v Upminster | The Cricket Green, Weybridge | Results |
| 15 Jun 2014 | Second Round | Blackheath v Old Rutlishians | The Rectory Field, Blackheath | Results |
| 15 Jun 2014 | Second Round | Aston Rowant v Cockfosters | The Butts Way, Kingston Blount | Results |
| 15 Jun 2014 | Second Round | Bromley v East Molesey | Plaistow Lane, Bromley | Results |
| 15 Jun 2014 | Second Round | Sawbridgeworth v Fives and Heronians | Town Fields, Sawbridgeworth | Results |
| 15 Jun 2014 | Second Round | Wanstead v Hertford | Overton Drive, Wanstead | Results |
| 15 Jun 2014 | Second Round | Ealing v Oxford | Corfton Road, Ealing | Results |
| 06 Jul 2014 | Third Round | Stanmore v Weybridge | Stanmore Common, Stanmore | Results |
| 06 Jul 2014 | Third Round | Richmond v Aston Rowant | Old Deer Park, Richmond | Results |
| 06 Jul 2014 | Third Round | Sunbury v Wanstead | Kenton Court Meadow, Sunbury-on-Thames | Results |
| 06 Jul 2014 | Third Round | Reigate Priory v Waltham | Park Lane, Reigate | Results |
| 06 Jul 2014 | Third Round | Bexley v Brentwood | Manor Way, Bexley | Results |
| 06 Jul 2014 | Third Round | Bromley v Colchester and East Essex | Plaistow Lane, Bromley | Results |
| 06 Jul 2014 | Third Round | Ealing v Blackheath | Corfton Road, Ealing | Results |
| 06 Jul 2014 | Third Round | Fives and Heronians v Harold Wood | The Paddock, Chigwell | Results |
| 27 Jul 2014 | Quarter-Final | Blackheath v Bexley | The Rectory Field, Blackheath | Results |
| 27 Jul 2014 | Quarter-Final | Harold Wood v Reigate Priory | Harold Wood Park, Harold Wood | Results |
| 10 Aug 2014 | Quarter-Final | Bromley v Sunbury | Plaistow Lane, Bromley | Results |
| 27 Jul 2014 | Quarter-Final | Weybridge v Aston Rowant | The Cricket Green, Weybridge | Results |
| 17 Aug 2014 | Semi-Final | Blackheath v Bromley | The Rectory Field, Blackheath | Results |
| 17 Aug 2014 | Semi-Final | Aston Rowant v Reigate Priory | The Butts Way, Kingston Blount | Results |
| 07 Sep 2014 | Final | Bromley v Reigate Priory | Corfton Road, Ealing | Results |
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