R1: Outlander wins quite easily. No question.
R2: Outlander wins in a short fight. Out-tiers him in skill.
R3: Outlander wins in a short fight Out-tiers her in speed / probably strength
R4: Outlander wins in a good fight. Outlander’s superiority is not that slight, but I believe Maul would give him what we can call a good fight.
R5: Outlander wins in a good fight.
R6: Stalemate, leaning Outlander. Both these characters are excellent duelists. I think they’re close in skill, but I believe the Outlander has the upper hand in force amp and most likely strength.
R7: Not sure atm.
R8: Anakin wins in a great fight. The Outlander will challenge Anakin, and he seems to have superior discipline and is less likely to make a mistake. So, the Outlander can definitely take a couple rounds, but Anakin should take the slight majority. When he gets pressured into defeat, Anakin will start using more of his potential and we’ll start seeing performances similar to the fight in the Invisible Hand.
An appeal to stone. Feel free to demonstrate Outlander's superior skill, if you want.
We already know both Mace and Dooku are his canonical superiors during their TPM days, and we know Obi-Wan is comparable to more skilled/powerful versions of the same characters. It's kinda hard not to see Obi taking it.