GODLIKE
Orlandu (FFT) vs. Sephiroth (FF7) - [EDIT] i'm an idiot. Okay, Orlandu still does get first go, but just barely. Sephy now just has to worry about 1.5x HE damage rather than 2x. Which is probably still enough to kill him on HP. Sephy's at least above PCHP but not *that* far above.
HEAVY
Reclaimer Dragon (WA4) vs. Meliadoul Tingel (FFT) - why the fuck did I nominate Reclaimer for Heavy again? Someone shoot me, this fight is unfair before Meliadoul gets screwed on her skillset's limitations. Rushing Beat has *really* high accuracy, to boot, so shield hype isn't very probable.
Nel Zelpher (SO3) vs. Margulis (XS2) - Nel has some skills that could feasibly hit widely enough to hit Margulis and his double, but...yeah, not confident enough to vote on this one.
MIDDLE
Crono (CT) vs. Roy (FE6) - This one, I'm not sure about. Luminaire can get around counters...but Roy can use SoS to heal, and attrition is one of Crono's worst enemies in any duel; if Roy gets at least two shots of healing with the SoS, that'll be enough to gas Crono. Three, and it's just unwinnable. Going to have to give this to Roy The Sword of Seals
Lich (FF1) vs. Chrom (FE:A) - feels like a pretty clear-cut FE Versus Status match.
Chameleon Man (WA3) vs. Byleth (FE3H) - [EDIT] Explaining in perhaps more concrete terms, while I do understand that Byleth has a counter-dodging skill, unless FE has developed something closer to Speed Save style reactions as of 3H specifically to be nulled by this ability, I see baseline FE counters as Countergrasp at best in theory, and probably something sub-Countergrasp in practice. To that extent, my decision holds.
LIGHT
Kain Highwind (FF4) vs. Maria Balthasar (Xenogears) - i can't believe I'm mathing this one out. Maria is not a healer, so Kain has no issue just bringing nothing but Jumps, for...what would be at best, 4HKO damage to average. Which 3HKOs Maria and goes first to Maria's utterly *abysmal* speed. To describe just how comprehensively Kain wins this, though.
Maria gets one shot of sub-average (literally magic pixels against average) magic damage, and then three shots of significantly-below-average physical damage, with Kain having above-average durability on both fronts. Graviton does about 29% of his health for the one shot it gets. Should she live that long, the three uses of Robo-Kick will do just short of 20%, leaving him at 10%. She can squeeze one more shot of damage with Robo Beam, which would in turn take Kain down to 4% health.
Maria would then still need 13 turns' worth of basic physicals to close that one out. She is not winning unless Kain literally sits there and does nothing.
Jogurt (ShF1) vs. Guile (CC) - THE DARK LORD SHALL TRIUMPH OVER PUNY--oh wait he took a point of damage nevermind.