During the 1898 war with Spain, then Lieutenant Winslow served on board the gunboat . He was commended for extraordinary heroism when, on May 11, 1898, he commanded a boat expedition from
Nashville and which succeeded in cutting two
submarine cables off
Cienfuegos, Cuba, which linked
Cuba with Europe. Despite enemy fire from point-blank range, which resulted in a bullet wound to his hand, Winslow retained command throughout the engagement. At that time, regulations did not allow Navy officers to receive the
Medal of Honor. However, all the enlisted sailors involved in the cable-cutting operation did receive the Medal of Honor. Winslow commanded from 1905 to 1907 and
battleship from 1908 to 1909. Winslow did not sail on the around-the-world cruise of the
Great White Fleet. When the fleet returned to the US in 1909, Winslow and
New Hampshire joined the fleet for its formal military review before President Roosevelt. Promoted to rear admiral on September 14, 1911, Winslow was Commander in Chief,
United States Pacific Fleet, from September 13, 1915 until July 29, 1916 when he was retired due to reaching the statutory age limit of 62. (While in command of the Pacific Fleet, he held four-star Admiral rank pursuant to a 1915 law that designated holders of certain commands to temporary 4-star rank; see
List of United States Navy four-star admirals.) Winslow was recalled to active duty in World War I with the rank of rear admiral. He served as Inspector of Naval Districts on the Atlantic coast until again retiring on November 11, 1919. While in this assignment, Winslow's flagship was , a private sailing yacht acquired by the Navy for use during the war.
Retirement Following the 1908 death of his oldest brother, Lt. Francis Winslow (II) USN, Rear Admiral Winslow became a member of the
Society of the Cincinnati in the State of New Hampshire, representing his direct ancestor Major General
John Stark. The admiral's younger brother, Arthur Winslow, also joined the Society, representing the General's oldest son, Major
Caleb Stark. Winslow was also a member of the
Military Order of Foreign Wars and the
Naval Order of the United States. ==Personal life==