In the last decade of the 15th century he was appointed tutor to Prince Henry (afterwards King Henry VIII of England). He wrote for his pupil a lost "Speculum principis," and Erasmus, in 1500, dedicated an ode to the prince speaking of Skelton as "unum Britannicarum literarum lumen ac decus." This Latin phrase roughly translates as "the one light and glory of British letters." In 1498 he was successively ordained sub-deacon, deacon and priest. He seems to have been imprisoned in 1502, but no reason is known for his disgrace. Two years later he retired from regular court attendance to become rector of Diss, a benefice he retained nominally until his death.