Godlike
Profound Darkness (Phantasy Star IV: End of the Millenium) vs Sephiroth (Final Fantasy VII): Best-case scenario for Sephiroth is that he doubles constantly after the first turn, and could kill in as few as eight of his own attacks? Opening with Wall of course, that would give PD only four turns to work with, and thus she could do something close to 2PCHP. Even then, though, that's enough.
Cloud of Darkness (Final Fantasy III) vs Reclaimer Dragon (Wild ARMs 4): Reclaimer absolutely does not 2HKO here. Rushing Beat should manage 0.71 by Tide's numbers once CoD's defences are taken into account, and I have CoD at 2.1 PCHP. You'd have to see her HP over a third lower for her to lose this. (or obviously something like a lower WA4 HP average)
Heavy
Rofel Wodring (Final Fantasy Tactics) vs Red (SaGa Frontier): We've seen this before. Rofel can win, but it requires seeing the RaySword as breakable, and... I think there was some other shaky judgement call which made me vote Red.
Athos (Fire Emblem: The Blazing Sword) vs Arnaud G. Vasquez (Wild ARMs 4): Illusion doesn't work on evadable magic in WA4, no reason it should work on evadable magic from FE. That said, Magic Blocker -does- work, which helps keep things interesting? But... no, wait, calcing things out, Luna still barely 2HKOs Arnaud. Arnaud could get lucky here with his ID or Magic Blocker kicking in quickly enough, but seeing as Athos has some evade of his own, criticals of his own, and always wins in 2 attacks while Arnaud may need many more, definitely have to side with Athos.
Middle
Yulie Ahtreide (Wild ARMs 4) vs Sara (Breath of Fire): Haste gives her way too many spare turns to work with.
Light
Anna (Fire Emblem: Awakening) vs Nei (Suikoden III): Anna's evade is too much, again. Nei even tanks through Levin Sword easily, but Brave Sword is good enough. Chances are that Anna will still be alive after 3 attacks despite being 2HKOed, which means she gets in three counters and two of her own attacks minimum.
Miriel (Fire Emblem: Awakening) vs Miranda (Grandia III): Miranda is fortunate she has GT physical damage. I'm not sold on Tremor hype (it's slow and hits the wrong defence), but Wowed techs 2HKO and Force Slash avoids the counter. I have to think that Wow -> Force Slash -> Dagger Dash ends up above average speed over 3 turns given how fast Dagger Dash is in particular.