Clifford rose in the world as an accomplished jouster, becoming Queen Elizabeth's second champion on the retirement of Sir Henry Lee. She made him a Knight of the Garter in 1592 and he sat as a peer in the trial of Mary, Queen of Scots. He turned to sailing as a career at some point, commanding a ship in the Anglo-Spanish War. He had little success during the war but was later renowned for his naval battles against the Spanish fleet, and particularly Spanish shipping, in the Caribbean. He help to set up an expedition with Walter Raleigh which led to the capture of the very rich carrack Madre de Deus off Flores in 1592. He had his own 38-gun ship built, the Scourge of Malice. He is famous for his short lived 1598 capture of Fort San Felipe del Morro, the citadel protecting San Juan, Puerto