In pursuance of a promise in 1383 on the part of the French to send support, both in men and money, to Scotland, Sir John de Vienne, admiral of France, was at last despatched, in April 1385, with two thousand men, fourteen hundred suits of armour, and the promise of fifty thousand crowns. Douglas was one of the nobles who welcomed Vienne on his landing at Leith in the beginning of May, and his share in the expedition which followed is vividly portrayed in the graphic narrative of Froissart. Though anxious as other Scotch border chiefs for the help of French allies, Douglas was not willing to take them on their own terms, or to yield the direction of the border war to foreign leaders. The numbers of the forces opposed, given by different authorities, vary even more than is usual in the narratives of war; but the English were largely in excess and better armed than the majority of the combined Scots and French army. The French knights were eager to fight, notwithstanding the disparity, but Douglas persuaded Vienne to follow the Scottish strategy of retreat and withdrawal of everything of value before the enemy advanced. The result was that Richard's raid, though it reached Edinburgh, resulted only in the burning of Melrose, Dryburgh, Newbattle, the church of St. Giles, and the houses of Edinburgh, but no victory or important conquest. Meanwhile the Scottish forces also declined to assail any strong fortress such as Carlisle and Roxburgh, still in the hands of the English, where a dispute between Douglas and Vienne prevented the prosecution of the siege. Vienne maintained that if it was taken it should be held for the French king, while Douglas refused to recognise the French in any other character than soldiers in the Scottish army. But a substantial advantage was gained by a sudden incursion subsequently made on the western English border, where the rich territories of the bishoprics of Durham and Carlisle yielded the Scotch more plunder than all the towns of their own kingdom. In this raid Douglas, along with his cousin and successor Sir Archibald, lord of Galloway, took part. The singular close of the French expedition was that the French knights and Vienne, weary of a war unproductive of honour or profit, and anxious to return home, were only allowed to do so on full payment of the subsidy of fifty thousand crowns promised by the French king. This appears from the receipt not to have been made till 16 Nov. 1385. The king himself took ten thousand as his share. Douglas received seven thousand five hundred. This sum, greater than any other noble's share, was probably due to the lands of Douglas having suffered most by the English. Another short raid of three days, in which Cockermouth and its neighbourhood were wasted, followed the departure of the French, and in this also Douglas took part.
His short life was made up of such raids. For the next three years little of note has been preserved. Its interest centres at its close in the famous battle of Otterburn, of which he was the victor and the victim. The Scotch, forewarned of the intention of Richard II, in the event of their renewing the war either on the east or the west borders, which had been the object in recent years of alternate attacks, to advance again into Scotland by the route left undefended, determined to check this policy by a simultaneous incursion on both of the marches. Having mustered their forces at Aberdeen, they were by a feint dispersed, only to reassemble on the north of the Cheviots at Yetholm or Southdean, near Jedburgh, to the number of fifty thousand. The great bulk of this large army under Sir Archibald Douglas was sent off to the west to ravage Cumberland and attack Carlisle, but a picked force of three hundred horse and two thousand foot, commanded by the Earls of Douglas, Dunbar, and Moray, was reserved for a diversion on the eastern border. So rapid was the movement of this force that it reached the neighbourhood of Durham before the English wardens were aware of its approach. It then retired on Newcastle, where it was met in the beginning of August by the levy of the northern counties, headed by the Earl of Northumberland's two sons, Henry Percy, to whom the Scots gave the name of Hotspur, and Sir Ralph his brother. In one of the skirmishes which took place near Newcastle, Douglas captured the pennon of Hotspur, and boasted that he would place it on the tower of Dalkeith. Hotspur declared it should not be taken out of Northumberland, and Douglas retorted that he might come that night and take it if he could from the pole of his tent. The Scottish force, which was on its way home, took the castle of Ponteland, but failed to take that of Otterburn, near Wooler, in the hilly parish of Elsdon, a little south of the English side of the Cheviots. It was an easy march across the Cheviots to the Scottish border; but Douglas, against the wish of some of the Scottish leaders, determined to entrench himself on the rising ground near Otterburn and give Hotspur the opportunity he had promised of trying to retake his pennon.
On the evening of 9 Aug. according to the English chronicles, on the 15th according to Froissart, on the 19th according to modern writers—in any case about the ‘Lammas tide