The very first challenge would come from Englishman James Ashbury, who raced against a fleet from the New York Yacht Club just off Staten Island in 1870. After much dispute over the conditions for racing, Ashbury’s Cambria finished tenth in the 17-boat fleet, prompting a second challenge the following year.
The 1871 America’s Cup match was a precursor for many of the legal battles that would engulf the Cup over the next 100 years. After reportedly consulting his lawyers, Ashbury insisted on racing against just one boat, not an entire fleet and protested both the scoring of the races and the Race Committee who set the race course. In the end he limped home complaining bitterly about poor sportsmanship on the part of the Americans and insisting he had actually won the America’s Cup, to no avail.
The next two Challenges came from Canada, but the northerners were no match for the Americans and were soundly beaten.