 In 1547, he was at the Battle of Pinkie Cleugh, but had the misfortune of being taken prisoner, and was detained till ransomed.In 1550, he went to France and entered the service of King Henry II as one of the "Gens d’Armes", under the command of the Earl of Arran.Thomas Crawford acquired the land and title of Jordanhill from Bartholemew Montgomerie (the chaplain of Drumry) following his return to Scotland from France with Mary, Queen of Scots in either 1560 or 1562.