In 1350 when Kanno Disturbance occurred, that was a consequence of the conflict in the Ashikaga family between Tadayoshi ASHIKAGA, a younger brother of Shogun Takauji, and KO no Moronao, a shitsuji (steward) of the Ashikaga family, Tokiuji at first supported Moronao and joined the coup d'etat for the rejection of Tadayoshi, but in December he escaped from Kyoto to belong to the Southern Court and obeyed Tadayoshi who had destroyed Moronao.
1350年、足利家において将軍尊氏の弟の足利直義と、足利家執事の高師直の対立が発展して観応の擾乱が起こると、時氏は初め師直を推して直義排斥のクーデターにも参加するが、12月に京都を脱出して南朝に属し、師直を滅ぼした直義に従う。