Beginning in late 1644 and again in 1645 Montrose conducted two campaigns winning in the course of them six battles. Against Covenanting militia at Tippermuir and Aberdeen in 1644 then in early 1645 at Inverlochy he routed Campbell forces under the Marquis of Argyll. In brilliant manoeuvres Montrose then won the battles of Auldearn, Alford and the crushing victory at Kilsyth in August 1645. However Charles I had been defeated at the Battle of Naseby in June and with the withdrawal of his Highland forces Montrose was defeated at Philiphaugh near Selkirk in the borders in September 1645 by Covenanting forces under David Leslie. Though he managed to flee the battle Montrose was later forced to escape to Norway in 1646.
After Charles I’s execution Montrose resolved to try once again to overthrow the Covenanting regime in Scotland so in Mar 1650 he landed with a small force on Orkney before crossing over to the mainland where unlike in 1644 he was treated with indifference resulting in few highlanders joining him as he moved south. In April 1650 he was surprised and defeated at the Battle of Carbisdale in Ross-shire and though wounded Montrose managed to escape but was later captured at Ardvreck castle. He was taken to Edinburgh where he was executed on the 21st May 1650.