In 1660 he accepted the head-mastership of Tonbridge School in Kent, but was appointed head-master of Merchant Taylors' School on 12 July 1661.
Chancellor was educated at Tonbridge School in Kent, England, where he was the bass player for a school band named Slice of Life and used to perform a cover version of Corey Hart's Sunglasses at Night in the dining room of his boarding house.
The poor house was provided by a trust set up by Sir Andrew Judd (benefactor of Tonbridge School on land in Back Lane (now Bank Street).
It has evolved into an educational and charitable institution, supporting schools such as Tonbridge School in Tonbridge, Kent; The Skinners' School in Tunbridge Wells Kent; The Judd School (also in Tonbridge) and Skinners' Academy in Hackney, London.
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He attended Tonbridge School from 1918 to 1921, and would later claim to have attended Christ's College in Cambridge.
Born in Tonbridge, Kent, Stewart was the son of Dr Haldane Campbell Stewart, who was also musical but in a different sphere - he was organist and choirmaster at Magdalen College, Oxford, the director of music at the Tonbridge School, Kent, and also notable as a cricketer on the Kent County Cricket Team.
The other schools respectively are the Sir Andrew Judd's free school (now called Tonbridge School), The Skinners' School and Sir Andrew Judd's Commercial School (now called The Judd School).