It is said that the Ogasawara clan in Awa belonged to the Southern Court in the period of the Northern and Southern Courts and many of the descendants became local clans serving the Hosokawa clan, the shugo of Awa in the Muromachi period.
阿波の小笠原氏は南北朝時代には南朝に属したとされ、その子孫の多くは室町時代には国人化して阿波の守護を務めた細川氏に仕えたとされる。