| 01 May 1999 | First Round | Upminster v Fives and Heronians | Upminster Park, Upminster | Results |
| 01 May 1999 | First Round | Basildon and Pitsea v Billericay | Mopsies Park, Basildon | Results |
| 01 May 1999 | First Round | Old Brentwoods v Woodford Wells | Ashwells Road, Brentwood | Results |
| 01 May 1999 | First Round | Epping v Hainault and Clayhall | Lower Bury Lane, Epping | Results |
| 01 May 1999 | First Round | Benfleet v Gidea Park and Romford | Woodside Park, Thundersley | Results |
| 01 May 1999 | First Round | Ongar v Saffron Walden | Love Lane, Ongar | Results |
| 01 May 1999 | First Round | Harlow v Loughton | Marigolds, Harlow | Results |
| 01 May 1999 | First Round | Southend-on-Sea v Wanstead | Southchurch Park, Southend-on-Sea | Results |
| 01 May 1999 | First Round | Harold Wood v Shenfield | Harold Wood Park, Harold Wood | Results |
| 01 May 1999 | First Round | Hutton v Wickford | The Polo Field Ground, Hutton | Results |
| 01 May 1999 | First Round | Old Southendian and Southchurch v Chelmsford | Southchurch Park, Southend-on-Sea | Results |
| 01 May 1999 | First Round | Buckhurst Hill v Hadleigh and Thundersley | Roding Lane, Buckhurst Hill | Results |
| 01 May 1999 | First Round | Hornchurch v Brentwood | Harrow Lodge Park, Hornchurch | Results |
| 01 May 1999 | First Round | Old Parkonians v Westcliff-on-Sea | Old Parkonians Association Ground, Barkingside | Results |
| 01 May 1999 | First Round | Brookweald v Horndon-on-the-Hill | Weald Park, South Weald | Results |
| 01 May 1999 | First Round | Stanford-le-Hope v Chingford | Stanford Recreation Ground, Stanford-le-Hope | Results |
| 01 May 1999 | First Round | South Woodford v Orsett | Highfield Road, Woodford Green | Results |
| 01 May 1999 | First Round | Ilford v Walthamstow | Valentine's Park, Ilford | Results |
| 08 May 1999 | Second Round | Westcliff-on-Sea v Chingford | Chalkwell Park, Westcliff-on-Sea | Results |
| 08 May 1999 | Second Round | not known v Ardleigh Green | not known | Results |
| 08 May 1999 | Second Round | Colchester and East Essex v not known | Castle Park Cricket Ground, Colchester | Results |
| 08 May 1999 | Second Round | not known v not known | not known | Results |
| 08 May 1999 | Second Round | not known v not known | not known | Results |
| 08 May 1999 | Second Round | not known v not known | not known | Results |
| 08 May 1999 | Second Round | Saffron Walden v Ilford | Anglo-American Playing Fields, Saffron Walden | Results |
| 08 May 1999 | Second Round | not known v not known | not known | Results |
| 08 May 1999 | Second Round | not known v not known | not known | Results |
| 08 May 1999 | Second Round | not known v not known | not known | Results |
| 27 Jun 1999 | Third Round | not known v not known | not known | Results |
| 27 Jun 1999 | Third Round | not known v not known | not known | Results |
| 25 Jul 1999 | Quarter-Final | South Woodford v Chingford | Highfield Road, Woodford Green | Results |
| 01 Aug 1999 | Quarter-Final | not known v not known | not known | Results |
| 01 Aug 1999 | Quarter-Final | not known v not known | not known | Results |
| 01 Aug 1999 | Quarter-Final | not known v not known | not known | Results |
| 15 Aug 1999 | Semi-Final | not known v not known | not known | Results |
| 15 Aug 1999 | Semi-Final | not known v not known | not known | Results |
| 30 Aug 1999 | Final | not known v not known | not known | Results |
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