The Handicap League Cup was awarded to the winner of a handicap league that ran from 1998 to 2013. Which team's players were assigned the most generous handicaps over these fifteen years? That would quite possibly be Maldon E - winning the trophy three times in 2000, 2008 and 2012.
The Team Handicap Competition has a long history starting in 1966, the second year of the league. No team comes close to Fambridge A who have won this trophy 8 times in the last fifty years. The closest are the distant Mapledene A, Woodham C and Woodham F who have won it 3 times.
Proving there must be some skill to winning handicap competitions, D. Newman (Maldon Wanderers) and M. Speight (Mayland) both won this competition 3 times but neither have been as consistent as Peter Ballard (Fambridge) who has vanquished all before him on 5 separate occasions.
Following careful consideration of the question, "how can more randomness be added to a handicap competition?", Handicap Doubles with partners drawn out of a bag was born. Maybe the most noteworthy winning pair was in the inaugural year of 1992/93 when father and son Martin and John Knights were drawn together and crushed all before them.