He taught 'kyuhotekiden' (a generic term given to Japanese archery, horsemanship, and etiquette and formal manners) of the Ogasawara school to Masamoto HOSOKAWA, who was a kanrei (deputy to the shogun) of the Muromachi bakufu (Japanese feudal government headed by a shogun), and this led him to serve Shogun Yoshimasa ASHIKAGA as a teacher of Japanese archery and to take charge of the Mushadokoro (a division in charge of guarding over a residence of a retired emperor or a cloistered emperor).
本家小笠原氏に倣って「糾法（弓法）的伝」（小笠原流）を室町幕府の管領細川政元に伝授した縁で、将軍足利義政の弓道師範、更に武者所を兼任するに至った。