He did the same with Kakazu's final form, Kimimaro Curse Mark V2 and Orochimaru's 8 Headed Serpent.
Oro's serpent head was more about illustrating the power of Itachi's legendary sword.
Kimimaro's Curse mark V2 withstood the best Gaara had to throw at him. At the time, I don't believe we'd ever seen such a display of raw power. Kimi lost, but it was clearly understood that he would've been the victor had he not died from sickness.
Kakazu.... If I remember correctly Naruto's 1st attempt failed, then Kakashi and Yamato had to step in. Kakazu and the Naruto/others both came up with strategies to combat the other, and Kakazu lost.