In 1572, Oxenham took part on the raid in Panama which was headed by Sir Francis Drake. In 1573 Oxenham was second in command, still under Sir Francis Drake, during the march to Panama. According to reports, Drake climbed a tree and saw the Pacific Ocean whereby he vowed: "besought Almightie God of his goodnesse to give him life and leave to sayle once in an English ship on that sea" At which Oxenham seconded: "protested that unlesse our Captaine did beate him from his company he would follow him by Gods grace".
During the raid, Drake and Oxenham split forces and tried two different approaches to Panama. Oxenham returned before Drake and set sail with two ships and 57 men, including John Butler.
Oxenham made his way to the Atlantic coast to prey on shipping. He spent the winters of 1576-1577 inland. In February 1577, Oxenham (in a pinnace which his men and some escaped African slaves, the Cimarrσnes built) via a river entered the Gulf of Panama. They looted the Pearl Islands where they tortured a Franciscan friar. From there they plundered two ships laden with gold and silver headed for Panama.
Leaving the Pacific, they were headed towards the Atlantic when they were attcked by the Spanish. Many of Oxenham's men were killed and the treasure was recaptured. Oxenham and some of his men escaped but were hunted down, captured and taken to Panama in April 1578. A total of 18 Englishmen plus 40 Africans. 14 of the Englishmen were hanged, the Africans were returned to slavery and Oxenham, Butler and Thomas Sherwell (all of whom were officers) were taken to Lima, Peru and executed late 1580.
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