Chikayoshi went up to Kyoto with MINAMOTO no Yoshitsune's force in October 1183 and reentered Kyoto on New Years Day, 1184 to perform various affairs as a local governor serving Yoritomo; he was also active as a negotiator with court nobles.
1183年（寿永2年）10月には源義経の軍勢と共に上洛し、翌1184年（元暦元年）正月に再度入京して頼朝代官として万事を奉行し、貴族との交渉に活躍する。