[1] He entered the United States Naval Academy in July 1865 and graduated four years later.

[2] He commanded the USS Fern at the Battle of Santiago de Cuba on July 3, 1898.

She died in 1899 while Winslow was serving as executive officer of the Naval Training Station in Newport, Rhode Island.

[1][3][4] He was a hereditary companion of the Massachusetts Commandery of the Military Order of the Loyal Legion of the United States by right of his father's service in the Union Navy during the American Civil War.

[1] He is buried with his father at Forest Hills Cemetery in Jamaica Plain, Boston.