Drury was named in many commissions in the county of Suffolk from 1486 onwards. Drury procured from Pope Alexander VI a licence for the chapel in his house at Hawstead, dated 8 July 1501 in the tenth year of that pontificate. The original is now in the museum at Bury. Another early reference to him is an indenture 15 December 1490 by which Robert Geddying, son and heir of John Geddyng, agreed with Robert Drury, esquire, for the erection of houses at Lackford, Suffolk, Roger and William Drury being co-feoffees.