In 1589, he took part in Francis Drake's English Armada, which sailed to Spain in an unsuccessful attempt to press home the English advantage following the defeat of the Spanish Armada, although the Queen had ordered him not to take part. In 1591, he was given command of a force sent to the assistance of King Henry IV of France. In 1596, he distinguished himself by the capture of Cádiz. During the Islands Voyage expedition to the Azores in 1597, with Walter Raleigh as his second-in-command, he defied the Queen's orders, pursuing the Spanish treasure fleet without first defeating the Spanish battle fleet.