- Winter Regatta - January 9&10, 1999
- Chili Cook-Off Race - February 6, 1999
- Edison Gulf Regatta - February 27&28, 1999
- Shrimp Festival Regatta - March 20, 1999
- Spring Fling Regatta - April 17&18, 1999
- Lady's Day Race - May 8, 1999
- Estebel Night Race - June 5, 1999
- Couples Race - July 19, 1999
- Firecracker Evening Race - July 17, 1999
- Sunworshipper's Race - August 21, 1999
- Summerset Regatta - September 4, 5&6, 1999
- Race to the Bridge - September 25, 1999
- South Seas Race - October 16, 1999
- NoBoca Race - October 30, 1999
- Festival of the Islands Race - November 20&21, 1999
- Commodores' Cup Regatta - December 11, 1999
