A small skirmish near Coldstream, on the Anglo-Scottish border, should have proved little trouble for Sir James Douglas, ‘the Good’ and ‘the Black’, who had recently been victorious at Bannockburn, and in his guerrilla-campaign to retake Border strongholds from the English. Sir James would, however, later call the Battle of Skaithmuir the most difficult fight of his long career.
The English were having difficulty getting supplies to their forces near Berwick (now Berwick-Upon-Tweed), Scottish forces having recently regained control of much of the area. Under Gascon knight Edmond Caillou, about eighty English soldiers rode therefore for Teviotdale, in search of cattle to steal. Receiving news of this, Sir James Douglas led his own men against the raiders. After a hard fight, Douglas won, and Caillou was killed. Two years later, the Scots would win control of Berwick, better-securing the area against future raids of this sort.