The Cayman Cup
Entry Fee
CI$35.00
Categories
Juniors
Cat 1-4
Women
Masters
Super Masters
Registration
Online ONLY
Deadline for registration is Oct 3rd
Course
East End Circuit
Race Partner
Get ready for Cayman’s premier cycling event!
The Cayman Cup will crown the best cyclist on Cayman’s roads in an all-out road race on loops of the East End Circuit. The overall winner will hoist the Cayman Cup and pull on the Cayman Cup Sunset Jersey as the fastest rider on the island.
Open to all athletes, category winners will be crowned in Men’s Categories 1-4, Masters (40-49), Senior Masters (50+), Elite Women and Juniors (under 18).
This one-of-kind event will feature the largest prize purse in local cycling with over CI$3,500 in cash and prizes!
OVERALL
1st
CI$500
2nd
CI$350
3rd
CI$250
4th
CI$150
5th
CI$100
CATEGORIES
1st
CI$100
2nd
CI$75
3rd
CI$50
4th
CI$35
5th
CI$25
The winner of the Cayman Cup doesn’t just take home the glory — they are awarded a timeless symbol of excellence.
Renowned for its exquisite craftsmanship and enduring prestige, the Waterford crystal vase awarded to the overall winner is elegant prize representing more than victory.
It reflects the clarity, resilience, and brilliance demanded by the Cayman Cup’s challenging course. Beautifully cut and internationally celebrated, the Waterford vase serves as a lasting reminder of a rider’s triumph in one of Cayman’s most coveted races.
Race Information
The race will be set on the East End Circuit, beginning at Clifton Hunter High School, continue towards East End, then down the back straight of Queen’s Highway and returning southward on Frank Sound Road.
Distance
18.7 miles (1 lap)
Juniors
Distance
37.4 miles (2 laps)
Women
Distance
56.1 miles (3 laps)
Men (All categories)
Registration
- Registration for the event will be online only via the form below.
- Your racing age is your age on the 31 December of the current year
- NO race day registration will be available.
