~1996~ May
- St. Thomas Yacht Club announces America's Cup Challenge
- 25 Founders provide seed capital to Syndicate.
- Entry fee paid; challenge confirmed by New Zealand.
- Peter Holmberg's world ranking jumps from 13th to 11th .
June
- Steve Morton signs as Vice President of Operations & Marketing.
September
- Topa Equities, Ltd. announces corporate sponsorship.
- Topa Equities (V.I.), Ltd. President, William S. Anderson, joins Board of Directors .
- Holmberg places fourth at World Championships of Match Racing in Croatia.
October
- Merchandise line of products introduced.
November
- Stars & Stripes `92 IACC Yacht purchased for training.
- Holmberg rises to 10th in world rankings.
December
- Arthur ``Tuna" Wullschleger named Logistics & Operations Coordinator.
~1997~ January
- Vitel Cellular announces corporate sponsorship.
- Cardow Jewelers announces corporate sponsorship.
- Knight Quality Stations Radio Group announces corporate sponsorship.
- The Ritz-Carlton, St. Thomas announces corporate sponsorship.
- $2 million raised locally in 30 days.
- New Zealand weather study & analysis initiated.
February
- David Pedrick/Pedrick Yacht Designs contracted as Principal Designer .
March
- Little Switzerland announces corporate sponsorship.
April
- Design Team Summit hosted at The Ritz-Carlton, St. Thomas.
- Crew trials begin locally.
- Seslia Securities announces corporate sponsorship
June
- Design & Technology Team meet in Newport, RI.
- Marine Program names Pauline Venzen-Dawes as Vice President.
July
- Holmberg wins Grade I Trofeo Match Race in Italy.
- Holmberg moves to 7th in world rankings.
- Coral World (V.I.) announces corporate sponsorship.
- Maximizer Technologies, Inc. announces corporate sponsorship.
August
- Holmberg wins Grade I Alandia Match Race, Finland.
- Holmberg moves to 6th in world rankings.
- Bluebeard's Castle announces corporate sponsorship.
- Holmberg steers Corel 45 Rush to IMS Championship, Division 1.
September
- Holmberg places 2nd in Grade I CIGNA Knickerbocker Cup, New York.
October
- Marriott Frenchman's Reef International Match Race announced for December 3-7, 1997 in Charlotte Amalie Harbor, featuring eight America's Cup skippers.
- Holmberg moves to 4th in world rankings.
- Bitter End Yacht Club signs on as Official Sponsor.
- Holmberg wins Bitter End Invitational Match Race.
- Texaco Caribbean announces corporate sponsorship.
November
- New Team Caribbean name and mark introduced.
- Caribbean Island Alliance (CIA) announced.
- Club Nautico de San Juan joins Caribbean Island Alliance.
December
- Team Caribbean hosts Grade I Match Race with 8 America's Cup Syndicates.
- Cellular One announces corporate sponsorship.
- Team Caribbean invited to Mini-America's Cup Regatta in New Zealand, April 1998.
~1998~ January
- Team Caribbean posts Performance Bond to the America's Cup Challenge Association and becomes one of sixteen (16) Challengers officially eligible for America's Cup XXX.
February
- Team Caribbean begins active training for Mini-America's Cup and crew recruitment.
- Team Caribbean hosts Official Puerto Rico launch at Club Natico de San Juan.
March
- Team Caribbean hires Puerto Rico support personnel and sails to San Juan for Heineken International Cup Regatta in Fajardo
September
- Hurricane Georges slams into US Virgin Islands
October
- George Plimpton hosts NYC Fundraiser
- Holmberg finishes 4th in Bermuda Gold Cup
November
- Holmberg travels to World Championships in Japan
December
- Team hosts 2nd Annual Grade I Frenchman´s Reef International Match Race
- Team begins discussions with Team Dennis Conner
~1999~ January 1999
- Team Caribbean merges with Team Dennis Conner
- Holmberg races VIM III in Key West Race Week
February
- Dennis Conner visits Virgin Islands to address community
- Team Caribbean Board of Directors form Team Dennis Conner Advisory Council
- New Team Store opens in International Plaza with co-branded gear
March
- Peter Holmberg wins match racing title at Grade I Congressional Cup in California
- Holmberg sails VIM III in SORC
- Team Dennis Conner begins boat building at New England Boatworks
- Hampton University sailing team visits St. Croix for week long training session.
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