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The next two centuries were beset by both external difficulties such as diminishing financial fortunes and failing buildings as well as internal strife between the various Members of the College.
The Official Visitor, the Archbishop of Canterbury, whose function was to ensure that the statutes were obeyed, was called in many times.
The lack of a disinterested body of governors and of any official connection to the Universities of Oxford or Cambridge contributed significantly to the school failing to fulfill Alleyn's vision in its first two centuries.
Some notable Masters did preside over the college during this time, including James Allen ( the first Master to drop the ' y ' from his surname ), who in 1741 made over to the college six houses in Kensington, the rents of which were to be used in the establishment of two small schools in Dulwich, one for boys from the village, the other for girls to read and sew, out of which James Allen's Girls ' School ( JAGS ) arose.
Dr John Allen ( 1771 – 1843 ) of Holland House was a most learned and influential man, but neglected the education of the Poor Scholars.

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