Fight that you want to see happen?

Upgraded Sakura vs Sasuke or Tobi >.>'

From characters that are still around and cannon: Kabuchimaru vs Anko

Kabuto was portrayed as being really skilled in the first series but he hasn't done much in Shippuuden. He's an expert psycho medic and his body is getting overtaken by Orochimaru, my favorite character.

Anko was Orochimaru's first apprentice and she was strong enough to survive the curse seal process. She was trained by Orochimaru and knows some forbidden techniques and she fights with snakes.

This fight would be excellent imo. Orochimaru's body vomiting is always cool to see and in this fight you've got two people who could be doing that all over the place. Both of them might be vomiting up scrolls and weapons as well. There'd be snakes flying all over the place and all types of disturbing stuff. On top of that, Anko has a curse seal so maybe she can grow wings or at least transform like Orochimaru's crew could.

From any Naruto character, filler or not:
Kabuto vs Sasuke (pre-Magic Star of David/Neutron Atoim Sharringan) vs Kimimaru vs Anko vs Guren vs Sound 4 vs Sai.

With Sasuke's power being limited to before he was super hacked by Itachi, I think this would be a pretty interesting battle where the winner gets to become one with Orochimaru

Anbu Reunion: Kakashi vs Teen Itachi vs Sai vs Yamato...

Super Obvious Kick Ass Battle: every Akatsuki member ever vs every akatsuki member ever

Battle of Sad Childhoods: Teen Orochimaru vs Gaara vs Neji vs an imaginary post timeskip Haku vs Naruto vs pre-super hacked Sasuke vs Sasori vs Sora

Battle of People Who Never Do Anything or Never Do Anything but Get Their Ass Kicked: Ino vs Anko vs Ten Ten vs Konahamaru vs Konahamaru's Crew vs Hinata vs Kurenai vs Iruka Sensei vs Sai vs Kankuro. Possible toss-ins would be Choji and Temari.

of the remaining characters, i most want to see sakura vs suigetsu because i think their interactions would be hilarious

Tsunade vs Jiraiya hahahah

Rock Lee vs. an open bar

or

Naruto vs Gaara during Chuunin Exams

pakkun vs gamakichi
yay.

Orochimaru + Sage Mode + No retarded handicaps anymore versus Madara.


You all know you would watch that.

jaraiya vs edo nagato, no 6 paths jutsu

The most obvious one, Naruto kicking Sasuke's ass!