Under his leadership, the Black Douglases continued their climb to pre-eminence in Scottish politics begun under his uncle, Sir James the Good, as well as their military dominance of the south of Scotland.

[4] Douglas went in the style of his uncle, the Good Sir James, and for the following few years waged a guerrilla war against the English in the Ettrick Forest and Jedforests.

Liddesdale, once in high standing with the Crown, had fallen into disfavour following his murder of Ramsay and another Knight, Sir David de Barclay.

[9][10] In 1355 the truce with England expired and Douglas with the Earl of Dunbar and March, whose lands had been ravaged, decided to attack Norham Castle in retaliation.

One of Douglas' captains, Sir William Ramsay of Dalhousie, was instructed to despoil, ransack and ravage the lands around Norham and burn the town in an effort to entice the garrison out to battle.

Following this Battle of Nesbit Moor, Douglas and March joined with the Earl of Angus along with French allies commanded by Sir Eugene de Garencieres took Berwick.

The Scots' scorched earth policy prevented raiding for supplies, and Edward had to turn homewards, but not before being ambushed and nearly taken by Lord Douglas's men outside Melrose.

[12][13] Following Edward's retreat into England, Douglas arranged a truce with William de Bohun, 1st Earl of Northampton that would last until Michaelmas.

Froissart states that "... the Earl Douglas of Scotland, who fought a season valiantly, but when he saw the discomfiture he departed and saved himself; for in no wise would he be taken by the Englishmen, he would rather there be slain".

King Edward III's son, Lionel of Antwerp, would have taken the Scottish throne, although the independence of Scotland was to be guaranteed, and a special clause was to be provided for the restoration of the English estates of the Douglas family.