1 frigate sunk 4 gunboats sunk All soldiers killed or captured
The Battle of Principe occurred on 19 June 1719 when a force of pirates led by Bartholomew Roberts and Edward Kenway attacked and destroyed the Portuguese fort of Santo Antonio on the island of Principe. Kenway had attempted to track Roberts and the slave ship Princess down to West Africa in the hopes of preventing Benjamin Hornigold's henchmen Josiah Burgess and John Cockram from capturing him, and Kenway and the crew of the Jackdaw sailed from the Caribbean Sea to Africa. They were greeted by a flotilla of five Portuguese Navy ships, consisting of the frigate San Carlos and her four gunboat escorts. The Jackdaw sunk all of the gunboats before boarding and plundering San Carlos, and the pirate ship proceeded to dock on the beach of Principe. There, they discovered the site of a Portuguese ambush that had left Captain Howell Davis dead, and Kenway decided to assist Roberts in freeing his men, taking over the fort, and killing Burgess and Cockram. Kenway managed to stealthily assassinate several guards before freeing the prisoners inside of the fort at Santo Antonio, and he also succeeded in killing Burgess and Cockram as they made preparations to leave the fort. The pirate crew of Bartholomew Roberts would take over the fort and raise the skull and crossbones, freeing the island from Portuguese rule. Roberts decided to turn to piracy and take Davis' place as captain of the Princess, and Roberts and Kenway agreed to work together in exchange for Roberts showing Kenway "the Observatory" in Long Bay, Jamaica.