Battle of Rio Nuevo ( 1658 ) The battle of Rio Nuevo occurred over two days on the island of Jamaica between Spanish forces under Cristóbal Arnaldo Isasi and English forces under governor Edward D ' Oyley . In the battle the invading Spanish were routed . It is the largest battle to be fought on Jamaica . Background . In 1655 , an English force led by Admiral Sir William Penn , and General Robert Venables seized the island , and successfully held it against Spanish attempts to retake it over the next few years . The battle of Rio Nuevo was one of these attempts , the other being Ocho Rios the year before . The Spanish were hoping to take back the island for the Spanish crown . The former Spanish governor of Jamaica , Don Cristóbal Arnaldo Isasi , attempted to recapture the island with forces from Cuba in the summer of 1657 , but the attack was repulsed by acting governor Colonel Edward D ' Oyley . Invasion . On 20 May Isasi attempted an invasion with more men recruited from New Spain ; the Tercios Mexicano ( Mexican Regiment ) . Isasi also had at his disposal four troop transports and a number of armed ships . In total the invasion force consisted of 31 captains , 31 ensigns , 28 sergeants and 467 soldiers . While this force anchored for two days near the mouth of Rio Nuevo , 3 English coast guard vessels chanced upon the Spanish but were chased away by gunfire . The English scouts however reported back to Edward D ' Oyley who mustered all available militia and soldiers that were fit to fight and were all assembled within a month . The Spanish in the meantime having fortified the area was joined by around 50 tattered Spanish guerrillas . Battle . On 25 June D ' Oyley mustered a total of 700 soldiers and militia and a total of ten ships with which to transport them . While they disembarked near the Rio Nuevo the Spanish transports were swiftly captured which as a result sealed off any major escape for the invaders . The Spanish seeing this , attempted to make a stand and repel the English behind their newly fortified redoubt . The English attacked and soon their firepower had a devastating effect . The Spanish were pulverized by cannon and firelocks in a pitched battle lasting two days . Suffering nearly two thirds casualties , the Spanish attempted to break out ; however most of those were killed or captured . What was left of the invasion force fled into the hills and jungle . They had lost over 300 casualties of which most were killed , the English had captured 150 prisoners , eleven flags , six guns and most of their arms and ammunition . English losses were around sixty men and most of the wounded on both sides however did not survive the tropical diseases . Aftermath . The victorious English conveyed the Spanish artillery back to ' The Point ' and Fort Cromwell installing it into their defences . Isassi tried to keep the struggle up until he was finally defeated in 1660 , finally having to escape Tower isle and flee to Cuba by canoe with his remaining supporters . The battle of Rio Nuevo was the last time the Spanish attempted to recapture Jamaica . The island would eventually be ceded to England by Spain in full in 1670 at the Treaty of Madrid .