Battle of Carrickfergus ( 1597 ) The Battle of Carrickfergus took place in November 1597 , in the province of Ulster in what is now County Antrim , Northern Ireland , during the Nine Years War . It was fought between the crown forces of Queen Elizabeth I and the Gaelic clan of MacDonnell , and resulted in a defeat for the English . Background . The north - east of Ulster was much fought over during the 16th century . Carrickfergus itself had been the base for a failed English attempt to colonise that corner of the province in the 1570s , but in the following decades the English influence gave way to the MacDonnells under the leadership of Sorley Bo y . In 1595 the central part of the province rose out in rebellion under Hugh O ' Neill , and the crown ' s only foothold was at Carrickfergus . The MacDonnells controlled the surrounding territory and adopted a wait - and - see policy , without committing themselves fully to the crown in its campaign to break the rebellion . In 1597 , the recently appointed English governor of Carrickfergus Castle , John Chichester , had enjoyed successes against the strongholds of the Clandeboye O ' Neills , and was negotiating with Sorley Boy ' s nephew , James MacSorley MacDonnell , over a series of raids and counter - raids in the locality . The Scots were aggrieved over certain cavalry operations that had lately been carried out in the governor ' s absence , and a parley was arranged for the 4th of November 1597 to hear their demand for reparations . The battle . On the appointed day MacDonnell was sighted by the English on his approach to Carrickfergus Castle at the head of an extravagant army , including 1 , 300 troops and 500 Scots musketeers . Not wishing to be outdone , the governor came out with the bulk of his men , just five companies of foot - who were wearied from a recent expedition - and one of horse . He led them out four miles , until the Scots were encountered , and then halted to allow his troops to close up on the advanced guard . In the interval the officers debated , one veteran urging the governor to proceed with the parley . But when his troops drew up , the governor turned to his commander , Captain Merriman , and said , " " Now , Captain , yonder be your old friends . What say you ? Shall we charge them ? " " Merriman assented , and was supported by the commander of the horse , Moses Hill . The order to charge was given , and the Scots fell back over the hilly terrain . But the English riders were not sure of their lead , and the governor was quickly isolated with a small party , which had managed to keep pace with him . On a counter - charge , the Scots surged around and broke the formation of the crown troops . The governor was wounded in the leg but tried to rally his men by remounting and charging down the slope . He was shot through the head and killed outright . Another officer was hit in the head and captured , another had his horse shot out , and another was shot through the shoulder . The crown forces were dismayed , and although reinforcements - including the sick , so depleted was the garrison - sallied out from the castle and prevented a massacre , the death toll on the English side reached 180 , with 30 - 40 wounded . Some managed to survive by swimming away in Larne Lough , with or without their horses , and fetched up on the shore of the peninsula of Island Magee . Aftermath . The English defeat was partly put down to a lack of gunpowder , but there was no attempt to excuse the crassness and ineptitude of the governor ' s conduct . Despite the size of the force he had chosen to bring to a mere parley , MacDonnell had little difficulty in justifying his own conduct . There was some irony in the Scots ' victory , because MacDonnell ' s uncle , Sorley Boy , had sacked the town over twenty years before in revenge for the English massacre of clan dependents on Rathlin Island .