Montrose supported Charles I when Scotland entered the English Civil War and, commanding a small army of Irish and Scottish irregulars, inflicted a dramatic series of defeats on the stronger Covenanter forces in the north (1644–45) before being defeated at Philiphaugh. After several years in exile, he returned to Scotland in 1650 in a bid to restore the new king Charles II, but was betrayed to the Covenanters and hanged.