He was a pupil at Magdalen College School, Oxford, where he probably studied under the grammarian John Stanbridge.
[4] About 1519 he presented Cardinal Wolsey with a verse and a prose treatise, with a dedication requesting patronage.
In the same year he published Libellus epigrammaton, an anthology of poems addressed to Wolsey, Henry VIII, Thomas More, and John Skelton.
His Vulgaria, published in 1520, pays compliments to the late king Henry VII, to Thomas Linacre, and to More, who was here first described as "a man for all seasons".
Whittington's grammars continued to be printed during the 1520s, usually by Wynkyn de Worde but briefly also by Richard Pynson.