Hugh was a clerk and one of the officers of the English exchequer, was employed in a matter arising from some wrongs done to the abbot of Ramsey in 1282; he was attached to the household of Eleanor of Castile, queen of Edward I, was her steward, and one of her bailiffs for the barony of Haverford.

In 1292 the king employed him to audit the debts due to his late father, Henry III, and in that and during the next three years he was the head of the justices itinerant for the northern counties.

In 1296 Edward appointed Cressingham treasurer of the kingdom, charging him to spare no expense necessary for the complete reduction of Scotland.

[1] The Lanercost Chronicle states the Scots dried and cured his hide and of his skin William Wallace caused a broad strip to be taken from the head to the heel, to make therewith a baldrick for his sword.The Scalacronica merely states that the Scots caused him to be flayed, and in token of their hatred made thongs of his skin.Walter of Hemingburgh recorded, The Scots flayed him and divided his skin among themselves in moderate-sized pieces, certainly not as relics, but for hatred of him.He is known to have left a daughter Alice, who married Robert de Aspale and had issue.

[2] In the 1995 film Braveheart Cressingham is portrayed by the actor Gerard McSorley, and dies by being beheaded by the Scottish rebel leader William Wallace.