Once the Battle of Shizugatake commenced, Yoshitsugu was said to have taken part within the Toyotomi ranks. What he did—if anything—is scattered among legends and folklore. One account states that he was the one who used his wits to convince Katsutoyo to surrender prior to the battle. Yet another tale depicts him as a brave warrior in the front lines, who performed many deeds with his magnificent spear. The "Hitosuyanagi Kaki" is famous for stating that Hideyoshi offered immense praise to both Yoshitsugu and Mitsunari for the battle, stating particularly for Yoshitsugu, "Ōtani Keimatsu was the participant who was excellent since the first move." However, this statement does not appear in other historical texts, so it is possible the quote is entirely fictional.