Verified answer

Unfortunately, we already know the answer to this question since, a new episode title was announced, Episode 654 : (Rival Decisive Battle! Satoshi Versus Shinji!!) (ライバル決戦！サトシ対シンジ!!). Therefore, Ash ( Satoshi ) will defeat Conway ( Kouhei ) and Paul ( Shinji ) will defeat Barry ( Jun )

No, because i didn't watch it. Unfortunately i stopped watching pokemon a long time ago, after they removed Misty (the orange haired girl) and changed the out-look of the newer pokemon's. It has been a disaster ever since and they still could have done a good job with it, but they recklessly ruined the plot, by making it into a franchise. However, i could see a possible come back, if they completely change the anime into a harem/ecchi type.

Hey, i don't think this aired yet, it should be coming out soon though. what website are you using to watch it?

I'm gunna assume that paul wins though, He is more ash's rival then barry is