Within his first year of marriage the young Nithsdale led a punitive
raid against Irish raiders who had been troubling the tenantry of his father's Fiefdom of
Galloway. In early summer 1388, with a party of 500 well prepared veteran
men-at-arms he sailed into
Carlingford Lough, landed outside the town and summoned their leaders. The chief of the townsfolk offered a sum for a temporary truce, to which Nithsdale agreed. Secretly the townsfolk sent off to
Dundalk for reinforcements, with which they were obliged. 800 spearmen from Dundalk surprised the Scots camp by night, and were supported by a
sortie from
Carlingford town. The Scots, veterans of years of brutal Border warfare, drove the Irishmen off, captured the town and burnt it, seized the Castle and captured 15 ships in the harbour.
En route back to Scotland Nithsdale "ravaged" the
Isle of Man. Nithsdale's expeditionary force sailed back into
Loch Ryan with enough time to join his father and the Earl of Fife and Menteith who had just led an expedition over the western marches into Northern England while a second army under James, 2nd Earl of Douglas, simultaneously led an expedition into England by the eastern marches, which culminated in the
Battle of Otterburn. == Feuding, Crusading and Death==