He was made master of the works at Windsor Castle in 1364[4] under Wykeham, in 1372 Edward III granted Wynford a pension of £10 per annum.
With the death of Edward III the new king Richard II of England favoured Wykeham, with newfound wealth he founded in 1379 New College, Oxford, which was designed by Wynford,[5] who also designed Winchester College[6] founded by Wykeham in 1382.
In 1389-90 he was repairing Winchester Castle, from 1392 he designed Wardour Castle, and in the 1390s[7] he commenced his last major work, the remodelling of the Norman nave of Winchester Cathedral in the latest Perpendicular Gothic style.
The two colleges also have cloisters that are next to rather than surrounded by the main college buildings, which form a separate courtyard consisting of as well as the great hall and chapel, an entrance gate with tower above, sets of rooms for scholars and fellows opening off staircases, a library, accommodation for the Warden.
There is a portrait of Wynford[8] in the stained glass in the east window of Winchester College; this shows an old man with thinning hair, a long nose and dropping moustache and forked beard with the words 'Willms Wynfort lathomus' below.