In the reign of Richard II (1377–1399) a king's licence was awarded to Baldwin de Radyngton in 1398 to found a chantry in Enfield at St Andrews parish church, endowed with lands to the value of £10 per annum.
His widow Agnes came to reside at Enfield and remarried, and the estate was put into Trust, with Lord Tiptoft as Trustee.
Within two years it had passed to one Richard Ingleton, and in 1471 he received a licence from Edward IV to endow a chantry at Enfield church with proceeds from the same estate, to the value of 10 marks.
[1] It is recorded that there was a schoolmaster at Enfield before 1524, since one is mentioned in connection with the funeral in that year of Sir Thomas Lovell of Elsing.
It therefore appears likely that this had been used for the chantry-school, and that its reformed activities were continued there under the new Grammar School foundation and endowment until new buildings were constructed under the William Garrett bequest of 1586.