1930 - Enterprise (USA) def. Shamrock V (UK) - 4 / 0

The aging Sir Thomas Lipton received a thrashing at the hands of another Vanderbilt, this time Harold S. "Mike" Vanderbilt, who became the first owner to sail his sailboat in America’s Cup competition. Enterprise (pictured left) defeated the Nicholson-designed Shamrock V by as much as nine minutes. Designed by Starling Burgess (son of Edward Burgess), Enterprise is renowned for its "Park Avenue" boom, The large, flat boom, wide enough for a crewman to walk its length, allowed a curve to be put into the foot of the mainsail, thus achieving a more aerodynamic shape.

1934 - Rainbow (USA) def. Endeavour (UK) - 4 / 2

Sir T.O.M. Sopwith, the British aviation pioneer, turned his technological ingenuity toward the water, challenging with what has been judged as the superior sailboat, the Nicholson-designed Endeavor. Indeed, like Lipton’s earlier series, Sopwith took a 2-0 lead over the NYYC’s Rainbow in the best-of-seven match. But the 128-foot American sailboat, designed by Edward Burgess’ son, Starling, won the next four races—including Race 4, marred by a controversial luffing incident, and Race 5 in which a crewman was fell overboard—to win the series. Clever tactics on the part of Vanderbilt’s crew and bungled opportunity on Sopwith’s part are credited with the American victory.

1937 - Ranger (USA) def. Endeavour II (UK) - 4 / 0

Sopwith returned in 1937 with Endeavor | (pictured right), but she proved no match for Vanderbilt’s Ranger, at 136-feet the largest "J" boat ever built. One of the most remarkable points of this defense was that it was the first of eight that involved the legendary Olin Stephens, of Sparkman & Stevens, as a designer. It was Stephens who pioneered and refined the use of towing tanks in sailboat design.