He attracted the notice of Lady Margaret Beaufort, countess of Derby, who made him comptroller of her household.
Baker says: 'The last chapel was Mr. Hugh Ashton's well known by his monument and his rebus upon it, a thing then much in fashion, and must be forgiven to the humour of the age.
It may, 'tis hoped, one day recover the right; and might I choose my place of sepulture I would lay my body there, that as I owe the few comforts I enjoy to Mr. Ashton's bounty, so I might not be separated from him in my death.'
'What was wanting in that more public capacity he made up and supported in his private station by founding four fellows, who were his chaplains, and as many scholars, together with an annual dirge to be observed for him on the day of his interment.'
According to Thomas Baker, who followed the inscription on his tomb at York, and copied in Queen Mary's reign by George Bullock, then master of St. John's, he died 23 November 1522, but C. H. Cooper and J. E. B.
'Hic situs est,' runs the inscription, 'Hugo Ashton archidiaconus Ebor., qui ad Christianæ religionis augmentum socios 2 ex Lancastria totidemque scolares, sociumque et scholarem Eboracensis sociumque et scholarem Dunelmensis diœcesis oriundos, suis impensis pie instituit, atque singulis a se institutis sociis consuetum sociorum stipendium solidis 40 adauxit.