The Cayman Islands competed at the 2000 Summer Olympics in Sydney, Australia.

The following is the list of number of competitors in the Games.^[1]

Men's Long Jump

• Kareem Streete-Thompson
  1. Qualifying – 7.99 (did not advance)

Women's 100m

• Cydonie Mothersille
  1. Round 1 – 11.38
  2. Round 2 – 11.81 (did not advance)

Women's 200m

• Cydonie Mothersille
  1. Round 1 – 22.78
  2. Round 2 – DNS (did not advance)

Women's Single Handed Dinghy (Europe)

• Tomeka McTaggart
  1. Race 1 – (27)
  2. Race 2 – (27)
  3. Race 3 – 25
  4. Race 4 – 25
  5. Race 5 – 25
  6. Race 6 – 23
  7. Race 7 – 21
  8. Race 8 – 22
  9. Race 9 – 27
  10. Race 10 – 25
  11. Race 11 – 24
  12. Final – 217 (26th place)

• Cayman Islands at the 1999 Pan American Games