Kakashi from Kakashi Hiden (doesn't have the Sharingan, but he obviously kept the over 1000 copied techniques, and now his chakra isn't constantly draining because of the Sharingan's use. He doesn't use Raikiri anymore, leaves him wide open, instead he uses Shiden). Summonings allowed.
Shikamaru from Shikamaru Hiden.
Jiraiya. Sage mode allowed. Summonings allowed.
Naruto (when we first see him in Part II. so we're talking Kazekage rescue mission levels). Can go into 1-> 4 tails mode. No Sage mode available. Summonings allowed.
Basically battle of the tag teams.
This came from me wondering how the hokage and his assistant would fare against Jiraiya. Naruto is only there cuz I wanted to give him a sidekick.
I think it would come down to who's the best between Kage Kakashi n Jiraiya, and how well the other do exel as support.
There are a couple of ways this battle can go.
First of all Kakashi wasn't always tired just because of the Sharingan, he has admitted and said it many times - his chakra pool is simply not that large. As to the actual battle - Naruto is extremely durable if nothing else, I am fairly certain his clones would at least tire either Shikamaru or Kakashi. Jiraiya could proceed to finish them off then. Even without SM he is no joke, Sannin are extremely strong. If he can summon Ma and Pa, it's game over. Bunta would be too huge for this kind of battle.
As to 4-tails Naruto he could probably solo them. Shikamaru could probably hold him with Shadow Possession for a couple of seconds, but Naruto would eventually break out of it. I don't know any Jutsu in Kakashi's arsenal that can pierce his 4-tails cloak.