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Sith team:

Luke Skywalker (Apprentice of Clone Palpatine)
Darth Krayt (reborn)
Mara Jade (Emperor's Hand)
Darth Revan
Darth Caedus

vs

Jedi team:

Luke Skywalker (Fate of the Jedi era)
A'Sharad Hett (Jedi Knight, as-of the end of the Clone Wars)
Mara Jade Skywalker (Jedi master, pre-Caedus fight)
Revan (turned to the light)
Jacen Solo (shortly after Vong war, pre-fall)




Both teams will find nothing odd about the fact that they're fighting themselves/turned versions of their loved ones.

Who comes out on top,

This is extremely lopsided, IMHO. Feat-to-feat, team 2 stomps.

In Team 1:

Krayt and Caedus are stronger then their previous incarnations.

In Team 2:

Luke, Revan and Mara are stronger then their previous incarnations.

-------------

I think that Team 2 has good chance.

I'll note that A'Sharad's a total load compared to his later incarnation (A'Sharad was a saber monkey. Krayt's much more experienced with sabers *and* a force beast), and Caedus was a fairly significant upgrade over Jacen.


In the other direction, Revan's two incarnations are relatively close.