Jackdaw vs. HMS Enterprise was a naval battle between the pirate brig Jackdaw and the British Royal Navy man o' war HMS Enterprise which was fought off Montego Bay, Jamaica in 1722 during the Golden Age of Piracy.
Pirate captain Edward Kenway set out from Havana, Cuba aboard the Jackdaw after upgrading his ship's hull and guns, and he decided to prey on British merchant shippping for a change. When Kenway spotted the Royal Navy man-of-war HMS Enterprise off Montego Bay, Kenway decided to close in for battle with the powerful warship. He immobilized the powerful warship before boarding it, killing 20 of its crewmen, and capturing the ship. Kenway seized 1,000 reales, 90 pieces of wood, 105 pieces of metal, 25 bags of sugar, 2 mortar shells, 5 fire barrels, and 7 new crew members, and he handed the ship over to his crew member Gest Uren, who became its new captain.