When Tadayoshi, supported by the Southern Court, gained a military advantage, Yoriharu sent his army to his territory, Awa Province, to oppose Tadayoshi, and tried to place local political powers under his control by various means, such as appointing the Atagi clan, which had a powerful navy in Kii Province, as a Jito (steward); however, he encountered opposition from families in the Ogasawara clan, and the conflict with the Ogasawara clan, which supported the Southern Court, continued until the generation of his son Yoriyuki.
直義が南朝に属して軍事的優位に立つと、頼春は対抗のために分国の阿波国へ下り、紀伊水軍の安宅氏を地頭職に任じるなど国人の被官化を行うが、一宮氏など小笠原氏一族の反抗にあい、南朝方に与した小笠原氏との対立は子の頼之の代まで続いた。