|Naruto Uzumaki vs Tsunade|
|Number of Times Fought||2|
|Aftermath||Tsunade questions Jiraiya about Naruto's knowledge of the Rasengan. (Round 1)
Tsunade kisses Naruto. (Round 2)
|Story Arc||Search For Tsunade Arc|
Naruto hears Tsunade dissing the Hokages and challenges her to a fight. Tsunade vows she only needs one finger. Naruto attacks Tsunade, but she splits the ground, leaving him off balance and flicks him in the forehead, but he uses his unmastered Rasengan to no avail. Tsunade then makes a bet that should Naruto master the Rasengan she'll give him her necklace, otherwise he gives her all his money.
Naruto insults Tsunade after she defeats Orochimaru and once again vows she only needs one finger, but Naruto is determined this time. She overwhelms him the same way she did in the first round, however instead of flicking him in the forehead, she kisses it and thinks to herself he is going to be a strong man and a great future hokage as well.