Sunday 2nd April 2000 - Witham Town F.C. U11's Division 2 League Cup Final Boreham - 4 v/s 6 - Hatfield Peverel
U12's Division 2 League Cup Final Burnham Ramblers - 4 v/s 1 - Woodham Athletic
U13's Division 1 League Cup Final Broomfield - 6 v/s 3 - Three Rivers
Sunday 9th April 2000 - Burnham Ramblers F.C. Under 11's Division 1 League Cup Final Fennlands United - 2 v/s 5 - Three Rivers
Under 13's Division 2 League Cup Final Mayland Youth - 4 v/s 2 - North Essex Wanderers
Under 14's K.O. Cup Final Burnham Ramblers - 4 v/s 5 - White Notley aet, F/T 3-3
Sunday 16th April 2000 - Witham Town F.C. U11's K.O. Cup Final Fennlands United - 6 v/s 2 - Hatfield Peverel
U12's Division 1 League Cup Final Dunmow Rhodes - 2 v/s 3 - Latchingdon Magpies
Sunday 30th April 2000 - Burnham Ramblers F.C. U9's Blackwater League Cup Final Maldon Saints Lions - 2 v/s 1 - Valley Green Lions
U9's Dengie League Cup Final Fennlands Leopards - 3 v/s 0 - Heybridge Vipers
U10's Blackwater League Cup Final Dunmow Rhodes Lions - 2 v/s 3 - Maldon Saints Lions
Sunday 7th May 2000 - Burnham Ramblers F.C. U9's Crouch League Cup Final Feering Falcons - 1 v/s 3 - Hatfield Peverel
U10's Dengie League Cup Final White Notley - 3 v/s 0 - Valley Green Bears
U10's Crouch League Cup Final Three Rivers Jaguars - 2 v/s 1 - Silver End
Sunday 14th May 2000 - Maldon Town F.C. Under 12's K.O. Cup Final Hatfield Peverel - 3 v/s 1 - Dunmow Rhodes
Under 13's K.O. Cup Final Broomfield - 4 v/s 2 - Three Rivers
Under 14's Div 1 League Cup Final Burnham Ramblers - 1 v/s 3 - White Notley
Sunday 21st May 2000 - Burnham Ramblers F.C. Under 11's Mark Watkins Memorial Cup Final Fennlands United - 2 v/s 3 - Three Rivers
Under 11's Millennium Cup Final Coggeshall Town - 0 v/s 5 - Maldon Saints
Under 12's Millennium Cup Final Dunmow Rhodes - 6 v/s 5 - Maldon Town Pumas Under 13's Mark Watkins Memorial Cup Final Broomfield - 3 v/s 1 - Valley Green Hotspurs
Under 13's Millennium Cup Final Burnham Ramblers - 7 v/s 1 - Scarlett Youth
