In 1489 the 5th Earl of Angus, Douglas's father resigned his lordships of Tantallon, Douglasdale, Liddesdale, Ewesdale, Eskdale, Selkirk, and Jedburgh Forest to the crown.
In his capacity of Warden he met with his English counterpart Lord Dacre at Canonbie to hear grievances and fix punishments.
On reaching the mustering point at the Ellemford, north of Duns, they joined with the largest and most modern army that Scotland had ever fielded.
A petulant Earl of Angus, having had his advice snubbed by King James, left the field and returned to Scotland, leaving the Master and his brother in charge of the Douglas contingent.
On noticing the Master of Angus still on horseback, he cried to him, "asking if it had been in the manner of his race to remain mounted while their sovereign fought on foot".
The master hit a raw nerve in James's chivalric mind and he replied "I dare fight upon my feet as well as you or any subject I have, and that without coat-armour or royal cognisance."