Following Lord Dunraven's two unsuccessful challenges for the America's Cup in 1893 and 1895, another contender stepped forward from the shadows determined to have one more try before the century ended. His name was Sir Thomas Lipton, the immensely wealthy tea magnate of Irish parentage, and his decision to mount a challenge in 1899 was one which came to dominate the rest of his life. In all, he would commission five successive yachts, all named Shamrock and each one larger and more powerful than her predecessor, over a period of thirty-one years and his desire to win back the "Auld Mug", as he liked to call the fabled trophy, became an obsession.
All this was still in the future in 1899 however, and Lipton chose William Fife, Jr., to design his first Shamrock. Built by J.I. Thornycroft & Co. on the Thames at Chiswick, she displaced 135 tons and measured 128 feet in length with a 24½ foot beam. A handsome cutter carrying 13,492 square feet of sail, she was constructed from bronze and aluminium plating on a steel frame and looked every inch a winner upon completion. An American syndicate headed by C. Oliver Iselin ordered their defender from 'Nat' Herreshoff and christened her Columbia. Displacing 103 tons, she was fractionally longer than Shamrock at 131 feet overall but carried slightly less sail at 13,135 square feet.
To skipper their respective boats, Lipton chose Archie Hogarth and the syndicate chose Charlie Barr, the latter an immediate advantage for the defenders such were his skills and reputation. The two yachts raced first on 16th October (1899) when Columbia romped home a full 10 minutes ahead of her rival. The second race next day was a disaster for Shamrock which failed to finish after her topmast and biggest topsail collapsed in high winds. Following an inconclusive encounter on the 18th, the final race took place on the 20th, with Columbia finishing 6½ minutes ahead of Shamrock. The challenger had put up a fine show nevertheless, and Thomas W. Lawson, the yachting historian, called this last match "the finest 15 mile run in international yachting history". True or not, it decided Lipton to keep trying four more times before his death in 1931.