Ōsaki Yoshikane served as a daimyō during the Sengoku period.  He served on behalf of the Muromachi bakufu as the Commissioner for the Oushū Region.  Yoshikane held the title of Junior Fifth Rank (Upper) and Master of the Eastern Capital Office.  He was the ninth head of the Ōsaki clan.

Yoshikane was born the son of Ōsaki Masakane, the eldest son of Ōsaki Norikane and eighth head of the Ōsaki clan.  (Masakane received one of the characters in his name from Ashikaga Yoshimasa, the eighth shōgun).  His childhood name was Hikosaburō.

At the time of his coming-of-age ceremony, he received one of the characters in his name from Ashikaga Yoshihisa (the ninth shōgun) and was given a long sword.  In 1488, when confronted with a rebellion in the Ōsaki territory, he temporarily relied upon Date Hisamune to escape, later suppressing the rebellion with the support of reinforcements.  He was considered lacking in the capabilities required of the head of a clan.

Yoshikane died in 1529 and was succeeded by his eldest son, Ōsaki Takakane.