1. John Cheshire was commissioned as a pilot officer on 17 December 1963, and was successively promoted to flying officer and to flight lieutenant.

1. John Cheshire was commissioned as a pilot officer on 17 December 1963, and was successively promoted to flying officer and to flight lieutenant.
John Cheshire was promoted to squadron leader on 1 July 1971, and to wing commander on 1 July 1977.
John Cheshire was appointed Commander of the Air Wing of the Royal Brunei Air Force in Brunei Darussalam in 1980, for which he was appointed an Officer of the Order of the British Empire in the 1982 Birthday Honours.
John Cheshire became the station commander at RAF Lyneham in 1982 and, after his promotion to group captain on 1 July, Group Captain Contingency Plans at Headquarters United Kingdom Air Forces.
John Cheshire went on to be air attache in Moscow in 1987, and was promoted to air commodore on 1 January 1988.
John Cheshire became Deputy Commandant of the RAF Staff College, Bracknell in 1990, and was appointed a Commander of the Order of the British Empire in the 1991 New Year Honours.
John Cheshire was promoted to air vice marshal on 1 January 1992, and appointed Assistant Chief of Staff Policy and Requirements at the Supreme Headquarters Allied Powers Europe.
John Cheshire was knighted a Knight Commander of the Order of the British Empire in the 1995 New Year Honours, and promoted to air marshal on 23 January 1995.
In retirement, John Cheshire was the Lieutenant Governor of Jersey from 24 January 2001 to 7 April 2006.
John Cheshire was appointed chairman of the Royal Air Force Charitable Trust in July 2008.
John Cheshire was married until the passing of his wife; he has a son and daughter, and three grandchildren.
On 22 April 2022, John Cheshire was recognised with a road being named in his honour at the Royal Brunei Air Force Base, Rimba in Brunei.