5) was laid down on 8 May 1896 at Baltimore, Maryland, by the Columbian Iron Works; launched on 8 May 1897; sponsored by Miss E. H. Hazel; and commissioned on 29 December 1897 at the Norfolk Navy Yard, Lieutenant John B. Bernadou in command.

During Winslow's seven-week sojourn at Norfolk, the armored cruiser USS Maine sank in Havana Harbor; and the United States began drifting steadily closer to war with Spain.

On 11 March 1898, Winslow steamed out of Norfolk and headed south to Key West, Florida., a base much nearer the probable theater of operations in the approaching conflict.

At this point, the commanding officer of Wilmington decided to take his ship, escorted by Winslow and Hudson, into Cardenas harbor in search of three Spanish gunboats reportedly in port.

Winslow marked shoal water to Wilmington's portside and, upon reaching a point about 3,000 yards (2,743.2 m) from the city, sighted a small, gray steamer moored alongside the wharf.

By 1335, Winslow reached a point approximately 1,500 yards (1,371.6 m) from her quarry when a white puff of smoke from the Spaniard's bow gun signaled the beginning of an artillery duel which lasted one hour and 20 minutes.

As Hudson began to tow Winslow out to sea, one of the last Spanish shells to strike the torpedo boat hit her near the starboard gun and killed Ensign Worth Bagley who had been helping to direct the warship's maneuvers by carrying instructions from the deck to the base of the engine room ladder.

But for a short voyage to Philadelphia in mid-October, Winslow remained inactive until early in 1901, first at New York, in a decommissioned status, and later at the Norfolk Navy Yard where she was officially listed as "in reserve."

Whatever the case, Winslow was recommissioned at the New York Navy Yard on 16 February 1906 and steamed south to Norfolk, where she was placed in the Reserve Torpedo Flotilla.

Sometime around October 1923 the USS Winslow, along with other decommissioned war vessels, was scuttled near Sagamore Hill, Oyster Bay on Long Island to form a breakwater.