Despite the smallness of his salary and other disadvantages, he raised the school from insignificance, and was the first to engage an assistant master.
He seems, however, to have unfortunately misunderstood the character of one of his best-known pupils, Edward Cave, whom he treated with undeserved severity, and eventually drove from the school.
[3] Holyoake was instituted to the rectory of Bourton-upon-Dunsmore on 30 June 1698, to that of Bilton on 31 August 1705,[4] and to that of Harborough Magna, all in Warwickshire, on 9 November 1712.
He died unmarried at Rugby on 10 March 1730 – 1731, and was buried in St. Mary's Church, Warwick, where may be seen a quaint Latin inscription written by himself, which he directed to be engraved to his own memory as well as to that of his father and grandfather.
He bequeathed £30 to the daughter of Widow Harris, 'his tripe-woman;’ the interest of £200 to the poor of Rugby after the death of his cousin, Elizabeth Holyoake; and all his books (since sold), together with the portraits of his father and grandfather (since lost), to Rugby School.