In 1564 he participated in a trading voyage to Guinea made by three ships that returned to England laden with Portuguese sugar and brazilwood acquired under suspect circumstances.
[2] Fenner commanded Dreadnought, a ship of 400 tons,[8] in Drake's successful raid on Cádiz in the summer of 1587, after narrowly escaping shipwreck off Cape Finisterre at the outset of the cruise.
[10] He clearly says Drake decided to raid Cádiz after meeting two Zealand (Dutch) ships off Lisbon on 16 April, as mentioned by Richard Hakluyt in his The Principall Nauigations, Voyages, Traffiques, and Discoueries of the English Nation.
[12] Fenner was a captain in the Royal Navy and a member of Lord High Admiral Howard's war council,[13] which directly advised Elizabeth I.
[15] After a failed attack on Lisbon, and few prizes taken, a hundred men a day were dying from their wounds, scurvy, or starvation, and their bodies were thrown overboard.
The historian David Loades notes that if Fenner was the same man serving in 1593 then he also married, being recorded as having a son who temporarily replaced him undertaking duties at Chatham.