Godlike
Jenna Angel (Digital Devil Saga) vs Sinspawn Gui (Final Fantasy X): Uh surely.
Belial (Wild ARMs 4) vs Spectral Keeper (Final Fantasy X): Spectral Keeper's counters are GT, but that's not good enough for me. Glyph Mines also seem like they might work but they aren't actually useful against anyone as crazy fast as Belial.
Elyon (Breath of Fire: Dragon Quarter) vs Yuna (Final Fantasy X): Elyon goes first, but is average speed after that. He can do his damage, which is good but won't OHKO Yuna (well, the physicals would if they all hit, but yeaaah no), or summon clones which Anima can OHKO. Don't... really think he can get past the aeons past that, if he can even slug down Anima.
Luis Virgil (Xenosaga Series) vs Luca Blight (Suikoden II): Luca can one-round the first form, but Virgil does get an attack off first, which will probably be Ether Bomb. He'll then need... three? turns to kill the second, with that evasion rate. This will give Virgil at least three more turns in this form, and 4 is possible. If it's three... Stab, then Eternal Storm twice for ~2100 for 2.27 PCHP. If it's four then obviously things get much worse and Luca just loses. I dunno. This is close. Kinda inclined to tiebreak for Virgil on the grounds that even his column flame slash (the only thing with an -argument- to hit Virgil) might not be seen as good enough here. Open to arguments though. Wish I had a good read on Luca's HP.
Heavy
Billy Lee Black (Xenogears) vs Phyress (Valkyrie Profile 2: Silmeria): Pretty sure Phyress could 2HKO while applying turn 2 stone at the very worst, and Billy can't do anything about that.
Delita Hyral (Final Fantasy Tactics) vs Levin Brenton (Wild ARMs XF): Uhhh I'll get back to you. Delita 2HKOs (and certainly isn't in -any- danger of being outslugged by Blast) and has some decent evade. Not sure.
Tengaar (Suikoden Series) vs Gilgamesh (Final Fantasy V): Yikes this quarter. Tengaar's kind of out of her league.
Hugo (Suikoden III) vs Velna (Legaia 2: Duel Saga): Unsure. Hugo has both damage types which is a huge help, and evade is a major boon against Acolyte's Fist and Striking End, which means Velna only wins decisively if both she and Vestra live on one turn and Hugo will make sure this never happens. Makes me lean towards Hugo.
Middle
Boyd (Fire Emblem Series) vs Mystic Knight (Final Fantasy V): Faster, Break Sword.
Maya (Legaia 2: Duel Saga) vs Lilly Pendragon (Suikoden III): Maya kinda overrated. She only barely survives an attack + a Gospelled attack after, and that's before SoM. So she Gospels then heals... but over the next two turns she'll need to recast Gospel on one of them or she starts getting 2HKOed through one turn of Gospel and one not (since Lilly will have SoM up), and she'll need to also use one turn to heal again. And... yeah then this conundrum repeats, since SoM is permanent. I don't see how she's going to make headway here. To make matters worse Lilly damage is rather spiky and may just kill at some point even if Maya executes a "perfect" plan I can't see. Maya really wants Gospel to last more than three turns.
Gaff Gafgarion (Final Fantasy Tactics) vs Flay Gunnar (Mana Khemia: Alchemists of Al-Revis): I guess timed cards let him overwhelm Gaf's game.
Jet Enduro (Wild ARMs 3) vs The King of Awesome (Super Mario RPG: Legend of the Seven Stars): Fear makes a mess of Jet.
Light
Quistis Trepe (Final Fantasy VIII) vs Emma Hetfield (Wild ARMs Alter Code F): Quistis gives Emma time to set up, probably.
Ilyana (Fire Emblem Series) vs Big Joe (Xenogears): No.
Irenes (Chrono Cross) vs Sneff (Chrono Cross): This was my kneejerk, and I see everyone voting this way anyway.
Krin (Suikoden) vs Tricia (Soul Nomad & The World Eaters): Right, bandits beat archers. Not something they needed in the DL.