He was educated in the household of Thomas Stanley, Earl of Derby with James Stanley, Bishop of Ely and his great friend, William Smith, Bishop of Lincoln and founder of Brazenose College, Oxford. He became chaplain to his patron's wife, Margaret Beaufort, Countess of Richmond and mother of King Henry VII, before being appointed Bishop of Exeter in 1504. He was joint founder, with his predecessor in this See, Richard Fox, of Corpus Christi College, Oxford. It was through Bishop Oldham, who foresaw the coming changes of the Reformation, that Fox was induced to found a college instead of a monastery, as he had at first intended. Oldham himself is better known for the founding of Manchester Grammar School in 1515.
Earlier examples vary the position of the keys and sword.