Sherwood was the son of the common clerk John Shirwod of York and his first wife, Agnes.
[2] He learned Greek from the scribe Emmanuel of Constantinople, in 1455; for which he was later commended in a letter from Richard III of England to Pope Innocent VIII.
[3][4] He was a papal lawyer, and then a diplomat, when he became the first permanent English ambassador, resident from 1479 in Rome.
[3][5] He built up a noted classical library, and gained the support of George Neville, Archbishop of York.
[8] He visited Rome twice more as ambassador: in 1487, with Thomas Linacre and William Tilly of Selling; and in 1492–3, when he died there.