In the Muromachi period, at the direction of Takauji ASHIKAGA, the 10th generation of the family, Nagahide OGASAWARA, compiled 'Sangiitto (a book about general knowledge for samurai)' together with the Ise clan and the Imagawa clan.
室町時代には、足利尊氏の命により、十代・小笠原長秀が伊勢氏、今川氏と共に「三議一統」を編纂。