The defender Vigilant signalled a new era for the America’s Cup and sailboat design. The 125-foot sloop was the first of six Cup defenders designed by Nathaniel G. "Nat" Herreshoff, known as the "Wizard of Bristol" (Rhode Island) and considered by many to be the father of modern sailboat design.

However, designer George Watson designed another fast sailboat in Valkyrie II. The five-race series was closely fought, with Vigilant scoring a come-from-behind 40-second victory over Lord Dunraven’s Valkyrie II in the second race.

The controversial series between William K. Vanderbilt’s Defender and Lord Dunraven’s Valkyrie ended officially as a 3-0 victory for Defender, designed by Nat Herreshoff.

However, Defender only won a single race, the first, on the water. As the two sailboats approached the starting line in the second race, the mainsail boom of the George Watson-designed Boat hit Defender’s topmast stay, which broke. Defender’s crew made emergency repairs, but could not overcome the handicap. The race committee reversed the outcome, however, disqualifying Valkyrie.

The angry Lord Dunraven blamed the incident on the large spectator fleet crowding around the starting line. In protest, he had his sailboat withdraw from the third race immediately after crossing the starting line, ending the series.

This series marked the entrance of Thomas Lipton onto the America’s Cup scene. But the outcome became a recurring nightmare for the beloved yachtsman from Britain. Lipton and his Shamrock sailboats challenged a record five times for the "Auld Mug," but left empty handed after each one.

The third in the legendary line of Herreshoff sailboats was the 131-foot Columbia, which sported a fin keel and 90 tons of lead ballast. The William Fife-designed Shamrock was a quick boat, but proved no match for Columbia, which was skippered by the renowned Charlie Barr.

Nat Herreshoff’s Columbia proved faster than any newer designs and was selected to defend the Cup a second time. Lipton, on the other hand, commissioned George Watson to design the 137-foot Shamrock II, and with her 14,000 square feet of sail, she looked like a winner.

But Columbia came from behind in all three races to take the series. The third race was the closest. Just two seconds separated the huge sloops as they crossed the finish line, but Columbia, the smaller of the two, had 41-second time allowance, giving her a 43-second victory.

It was no accident that the defense syndicate headed by two of the biggest names in U.S. industry, Cornelius Vanderbilt and William Rockfeller, built the largest sailboat in the history of the America’s Cup. Herreshoff was again commissioned to design and build it, launching the bronze-and-steel sloop Reliance.

The massive sailboat was 143 feet long, had a 116-foot boom, and carried in excess of 16,000 square feet of sail. And again Lipton’s sailboat, this time Shamrock III, was out-matched, losing the last race by such a large margin that she was forced to retire before finishing.

Lipton’s fourth challenge, the one he came closest to winning, was postponed six years because of World War I. But it seemed worth the wait.

Armed with his Charles Nicholson-designed Shamrock IV, Lipton thought he had the Cup at last after his shamrock sailboat won the first two races over the NYYC’s Resolute. The third race Shamrock IV also won boat-for-boat, but the 107-foot sailboat won on handicap.

In the final two races, the Herreshoff-designed Resolute was not seriously challenged. The Cup remained in NYYC.