In addition, he and Nobumitsu TAKEDA, Yukiuji UNNO and Shigetaka MOCHIZUKI were called 'the big four in the archery and equestrianism' and he became the grand master of Kyuho (manners in time of peace and campaign strategy in times of war; Japanese horse-back archery technique) founded by MINAMOTO no Yoritomo when he was 26 years old; with these activities he built the base of the Ogasawara clan as shogunal retainer of the Kamakura Shogunate.
また武田信光・海野幸氏・望月重隆と並んで「弓馬四天王」と称されて、26歳のときに源頼朝の糾法（弓馬術礼法）師範となるなど、鎌倉幕府の御家人としての小笠原氏の基礎を築いた。