1914
Shamrock IV is the first of four challengers designed and built by Charles E. Nicholson. The unconventional looking yacht is nicknamed "ugly duckling", after the popular song. The fourth of Lipton's challengers is launched on May 26.

On July 18, under the charge of Captain Turner, Shamrock IV, leaves Portsmouth for the United States under tow by Lipton's steam yacht, Erin.

On August 7, Colonel Neil, in charge of Erin, receives a message announcing the start of hostilities between Germany and England. He is given an order to sail to the nearest British port, Saint George in Bermuda, where the two boats arrive on August 9.

Shamrock IV reaches New York on August 13, but the America's Cup is postponed.

1915
Shamrock IV is dry-docked at Robert Jacob's Yard, New York. When hauled, its hull is hidden by canvas.

1919
Lipton confirms his challenge for July, 1920.

1920
In February, Shamrock IV narrowly escapes being destroyed by a fire that ravages the Jacob shipyard.

Shamrock IV is re-launched at City Island on May 28, after being refitted. Charles E. Nicholson had redesigned the bow, accentuating the U-section in the same way as a scow. It is built in England and sent to City Island, where it is fitted onto the old structure.

Aware of the time penalties and the size of the wetted surface, Nicholson reduces the ballast by three tonnes and shortens the keel. He also replaces the centerboard with a lighter one.

From June 9 to 30, Shamrock IV sails with the original Shamrock, Lipton's favourite yacht, a 23-metre Fife III design, built in 1908.

After measurement on July 12 and 13, it is discovered that Shamrock IV has to give the New York Yacht Club defender, Resolute, designed by Nathanael Greene Herreshoff, seven minutes and one second, seven minutes and 15 seconds or six minutes and 40 seconds, depending on the challenger's rig configuration over a 30-mile course.

The America's Cup

July 15 to 27, 1920, off New York, United States.

Shamrock IV competes against. Resolute in the best of five race series.

There are two alternating race courses:
One is 15-nautical miles to windward off Ambrose Channel Lightship and return, a total distance of 30-nautical miles.
The other is an equilateral triangle off Channel Lightship, a total distance of 30-nautical miles.

Results

- July 15, first race, 30 mile windward-leeward course: Shamrock IV beats Resolute. Resolute does not finish after breaking her mainsail halyard.
- July 20, second race, 30 mile triangular course: Shamrock IV beats Resolute by two minutes and 26 seconds on corrected time.
- July 21, third race, 40 mile windward-leeward course: Resolute beats Shamrock IV by seven minutes and one second on corrected time.
- July 23, fourth race, 30 mile triangular course: Resolute beats Shamrock IV by nine minutes and 58 seconds on corrected time.
- July 27, fifth race, 40 mile windward-leeward course: Resolute beats Shamrock IV by 19 minutes and 45 seconds on corrected time.

Resolute beats Shamrock IV by three wins to two.

In August 1920, Shamrock IV is dry-docked at Robert Jacob yard at City Island, New York and remains there for several years.

1932
On Lipton's request, Shamrock IV is broken up

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