[2] Oldham left the Whitgift School in 1678 and took up the post of tutor to the grandsons of a retired judge, Sir Edward Thurland, in the vicinity of Reigate in Surrey.

It was during this period that he composed and had published his satires against the Jesuits,[3] at a time when popular anger was being stirred up against Catholics in England by the "Popish Plot".

In 1680, he became, for a short time, tutor to the son of Sir William Hicks, through whom he made the acquaintance of the notable physician Dr. Richard Lower.

He entered fashionable society (said to be centred on Will's Coffee House), and was approached by the Earl of Kingston-upon-Hull to be a private chaplain to his household.

The Earl of Kingston-upon-Hull had a monument, possibly designed by Grinling Gibbons, erected over Oldham's grave in St Edmund's Church, Holme Pierrepont.