By then, Dacre had secured the entire Greystoke inheritance, more than doubling his income and transforming himself from a minor border baron into a powerful northern magnate.
He also attended the wedding of Margaret's older brother, Arthur, Prince of Wales to Katherine of Aragon.
Dacre and his forces served under Thomas Howard, Earl of Surrey at the Battle of Flodden (9 September 1513), where the invading army of James IV was crushingly defeated and its king killed.
King James IV himself had been killed, and the Kingdom of Scotland then ceased its involvement in the War of the League of Cambrai.
Dacre later wrote that the Scots, "love me worst of any Inglisheman living, by reason that I fande the body of the King of Scotts.
In 1515, Margaret was banished from Scotland by the regent, John Stewart, Duke of Albany, and wanted to come to England with her second husband Archibald Douglas, 6th Earl of Angus.
Being heavily pregnant at the time, Margaret and her husband left Scotland with Dacre offering her Harbottle Castle in Northumberland, which he owned, as a place for them to stay.
[7][8] Dacre organised repairs at Wark Castle in 1517 obtaining money from Cardinal Wolsey and employing the Master Mason of Berwick to design new fortifications.
He was present, with all the other Garter Knights, at the meeting in 1520 between Henry VIII and Francis I of France now known as the Field of the Cloth of Gold.
Dacre was at the burning of Jedburgh in 1523, and with Arthur Darcy and Marmaduke Constable led a force to capture and slight Ferniehirst Castle which belonged to a personal enemy.
[10][11] Dacre died on the borders on 24 October 1525, killed by a fall from his horse, and was buried in his family's mausoleum at Lanercost Priory.