William, the 1st Earl, Archibald the Grim and both his son the 4th Earl and grandson, the 5th Earl fought in France as well as the along the Anglo-Scottish Border, during what would become known as the Hundred Years War. The 1st Earl and the 3rd were both present at the Battle of Poitiers, and the future 5th Earl Archibald, Earl of Wigtown was a deputy of John Stewart, Earl of Buchan at the Battle of Baugé and elsewhere. Archibald Douglas, 4th Earl of Douglas, had fought at Homildon Hill, was captured there and then joined the rebel Northern English Barons to fight at Battle of Shrewsbury where he was again captured. It was during this episode of his life that Douglas makes an appearance as one of the characters in William Shakespeare's "Henry IV, Part 1". In 1423 Douglas's son Wigtown, returned to Scotland to raise more troops for the French war and managed to enlist his father's support, the 4th Earl sailed for France with an army some 6,500 strong, was created Duke of Touraine and Lieutenant General of France by a grateful Dauphin. Douglas was killed at Battle of Verneuil in 1424. The 5th Earl of Douglas upon his accession was sometime regent of Scotland during the minority of James II of Scotland and Lieutenant-General of Scotland.