Along with the Prince of Wales, one of the most passionate yachtsmen of the 1890s was the 4th Earl of Dunraven. Determined to wrestle the America's Cup away from the custody of the New York Yacht Club before the end of the nineteenth century, he commissioned the great G.L. Watson of Glasgow to design him a winner worthy of the name and thus was conceived Valkyrie II. Rigged as a cutter and displacing 95½ tons, she measured 117½ feet in length with a 22½ foot beam and carried 10,042 square feet of sail. Built by D. & W. Henderson at Partick, alongside the legendary Britannia then under construction for the Prince of Wales, Valkyrie (II) proved a formidable challenger for the America's Cup and, despite her failure, returned home to considerable acclaim. Sadly, her life was cut short when she was sunk in a memorable collision with the yacht Satanita at the Clyde Regatta in July 1894.
To defend the America's Cup in 1893 however, a syndicate headed by Oliver Iselin had commissioned the equally talented Nat Herreshoff to design and build them Vigilant which, whilst her dimensions matched Valkyrie's extremely closely, had the initial advantage of carrying 11,272 square feet of sail against the challenger's slightly smaller square footage. Valkyrie (II) made the Atlantic crossing in September 1893 and the first race took place on 7 October. Vigilant won by 5 minutes 48 seconds and took the second race by 10 mins. 35 secs. on the 9th. The third and final race, scheduled for Friday 13th, was destined to become one of the most hotly contested in the history of the America's Cup and was won by Vigilant with the narrowest of margins, a lead of only 40 seconds. The New York Times called it "probably the greatest battle of sails that was ever fought" and the closeness of the finish determined Dunraven to try again in 1895.