In this period, it faced difficulties because it was deprived of some of its lands and had some of its collection of books carried away to Kyoto by Hidetsugu TOYOTOMI., who loved old books.
学校の財源であった所領が奪われ、古典籍を愛した豊臣秀次によって蔵書の一部が京都に持ち出されるなど、この時期の足利学校は困難に直面した。