In the 14th century the family were close allies of the Earls of Douglas, to whom they were squires, and about the end of that era they are first defined as Hoppringle of that Ilk, holding the lands of Earlside in Lauderdale. Descendants were much in evidence at the Courts of James IV and V, at least two being trumpeters in the tail of James IV and one falling at his side at Flodden in 1513. For 100 years, from about 1489, a succession of Pringle ladies, usually younger daughters, were Prioresses of the Convent at Coldstream. The association of Pringles with the woollen industry may be traced to 1540 when one of their name held the responsibility for overseeing the shearing, storage and transportation of the wool from the King's sheep. In 1592 various Pringles appeared before the King, with other Border lairds, giving an oath to faithfully serve the Wardens of the East and Middle Marches, and evidence of their extended land-holdings is shown by no less than six cadet families standing surety, one for the other, in keeping the peace. Five years later, Pringle of that Ilk and Pringle of Smailholm subscribed to a Bond of Manrent, taking it upon themselves the burden of ensuring the good behavior of Pringles in general. The last Pringle of that Ilk died in 1737, after which the principal family became the Pringles of Stitchill, the lands of which were acquired c.1630. Of this latter house, Sir Robert was created a Baronet of Nova Scotia in 1683 and, although the lands have now been sold, the Baronetcy has survived into the 21st century.