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Episode 1 Padawan Obiwan against Episode 2 Padawan Anakin

Both are serious and want to win by any means neccecary.
Fight in Cloud City (no civilians), anything goes.
Start facing each other with sabers in hands, eight feet apart.

This has been done more than a couple of times before.

Anakin wins, but it won't be easy.

Anakin is better. He's much stronger with the Force and is a slightly superior duelist. He does have issues though. Kenobi has a chance, but if Anakin plays his cards right he should have it.