He was a commissioner for settling border differences nominated by the treaty of Nottingham, 22 September 1484; his safe-conduct into England being dated on the ensuing 29 November.
He had encamped at Gartalunane, on the south bank of the Forth, in the parish of Aberfoyle, but during the darkness of the night of 11 October was surprised and utterly routed by Drummond.
[4] In 1514 Drummond gave great offence to many of the lords by promoting the marriage of his grandson, Archibald Douglas, 6th Earl of Angus, with the queen-dowager Margaret.
The Lord Lyon King of Arms (Sir William Cumming (or Comyn) of Inverallochy) was despatched to summon Angus before the council at Stirling Castle, when Drummond, thinking that he had approached the earl with more boldness than respect, struck him on the breast.
In 1515 John Stewart, Duke of Albany, was chosen Regent of Scotland, but because Drummond did not favour the election he committed him (16 July) a close prisoner to Blackness Castle, upon an allegation that he had used violence towards the herald.
With other lords he signed the answer of refusal to Henry VIII, who had advised the removal of Albany, to which his seal is affixed, 4 July 1516, and in October he announced his final separation from the queen's party.