The Chesapeake Grand Prix Regatta was designed as a showcase of America's Cup teams and close competition was the result. Team Dennis Conner was represented by helmsman Ken Read with Peter Holmberg calling tactics. They sailed aboard Chessie Racing owned by George Collins. Chessie Racing was the home town favorite at this regatta, with a boat of the same name carrying the flag for the Baltimore and Annapolis area around the world in the last Whitbread Around the World Race.
Members of four U.S. teams raced aboard five identical One Design 48 yachts, and to give focus to the races, Russell Coutts and members of Team New Zealand sailed aboard a sixth boat.
The first nine short races were sailed over three days. Coutts and his team showed why they are ranked as some of the best sailors in the world with consistent first place finishes marred only by one third and a 5th due to a penalty.
Winning the final long distance race on Sunday was a consolation for Chessie Racing. The two members of Team Dennis Conner and the rest of the crew had sailed well against the other U. S. teams but just could not match consistent sailing of the visiting New Zealanders.
The final results were: Numbers, sailed by Russell Coutts and Team N.Z. first, Chessie Racing with Read and Holmberg of Team Dennis Conner second, and Prime Outlets, helmed by Terry Hutchinson of AmericaOne out of San Francisco, third.