Don't see how Sasuke can lose either of those. He definitely wins S1 with mid difficulty, and the lack of CS in S2 won't be that much of a change - Hyuuga's only way of beating him is in close combat with an attempted 64-palms to shut down his chakra system, which would only result in a Chidori Nagashi and a blade running through them when they're stunned, not to mention that Sasuke is much faster than either of them - can't see Hinata having at least Tobi's reactions to avoid a blitz when he gets close, especially since she got saved by Naruto against 3 WZ clones.
Granted, genjutsu is a non-factor to either of them since they can just close their eyes and fight normally, plus Sasuke will most likely get hit once by Air Palm and some of his attacks will get deflected by Kaiten, but that's that. He can later just avoid it or encase himself in a snake (not Aoda or Manda, the one that tanked Deidara's explosion), so Sasuke wins both scenarios.