I'm pretty sure that would be damn near impossible.
1st Hokage defeated Uchiha Madara, I think that's already a testament to the incredible strength he wields.
Then you have the Second, who is said to have the greatest combat ability of any ninja EVER and also one of the greatest water users ever.
It would be almost impossible for Itachi to win.
The only real hope he would have is if he activated Susanoo.
Then, maybe, he could win, but it would still be a long shot.