Dark King (Final Fantasy Mystic Quest) vs Evrae (Final Fantasy X)
Heck no to Evrae ignoring the conditions of his own fight that make it easy in-game. He can't use the immunity-ignoring Slow on turn 1 - well until Dark King attacks him, but Evrae is faster. Dark King attacks & asks Cid to move the airship back which will happen by turn 2, meaning Evrae is only at short range for his first attack, then peppers Evrae with magic while Evrae uses his mighty 5HKO (which is even worse in game!) and still can't use the Slow because now he's stuck at long range. Eventually Evrae unlocks the "force close range" ability at 33% health but he's far too close to death by then, especially since his Slow move has crap damage attached, not to mention that DK can ask for the airship to be sent back to long range anyway. A slaughter.
Heavy
Basilio (Fire Emblem: Awakening) vs Lilka Eleniak (Wild ARMs 2)
Elf's stat topic claims Basilio has a 0% crit rate alone vs. average endgame enemies. WA2 luck is random, so I guess if Lilka enters the fight with the bad luck to have, uh, bad luck, Basilio can win, but otherwise Quick -> spam healing forever until misses or until Basilio breaks his weapon.
EDIT: Killer Axe, right. (Less TB speed-for-doubles hype here, Lilka doesn't get her first double until like turn 5, so Basilio has like 8 crit chances if Killer Axe's regular hit is heal locking anyway.)
Middle
Kloe (Legend of Heroes: Trails in the Sky) vs Lexis (Lufia II: Rise of the Sinistrals)
Battle of the slow status flingers with healing... but Anti-Sept messes with Lexis fiercely. He apparently has 3 different weapons to equip with 3 different statuses to threaten Kloe with, but chaining them requires building up a lot of IP... which Kloe might give Lexis in fairness while slinging Shadow Spears hoping for ID. And Kloe has 2 accessory slots anyway, so she probably blocked the one IP status Lexis could equip anyway.
EDIT: Wait, Lexis can block silence. But does it matter? What's his game here? He can't block ID without casino stuff that isnt' available until he leaves, so no. He can heal but eventually Shadow Spear will get him, although granted, if he equipped the right status weapon, he's likely to have time to get to 100% IP and do some kind of nasty status chain. Although maybe Radiant Plash can interrupt it? Eh, stickign with the vote for now.
SECOND EDIT: Okay, never mind, super said that Lexis can't block silence, so this is much more straightforward. (Tide claimed in chat that Lexis could block Silence....)
Light
Maribelle (Fire Emblem: Awakening) vs Maria Balthasar (Xenogears)
On the one hand, Robo Kick is physical damage. On the other hand, it still doesn't OHKO the insanely bad Maribelle, and she can use her oh-god-never-use-this-in-game War Cleric form for Renewal hype. Ugh, one of the cases allowing form choice is weird, for all that War Cleric might actually be better for her in Light in the DL (Maribelle loses all slugfests anyway, so might as well cheese some characters with regen.)
Olivya Phoraena (Tactics Ogre: Let Us Cling Together) vs Shady Thousand (Wild ARMs 3)
Aw yeah, TO cleric heal-chains.
Event #14: Being Charlie Brown- David Xanatos (Gargoyles) vs Erim (Lufia Series)
Erim is better at "being Lucy" but the fact that she loses constantly, forever, and will continue to lose in future Lufia games, has a certain timeless air about it. (Why can't you reform the Sinistrals and make them a wandering singing group of troubadours?) I can easily see Erim accepting this cycle of losses as the natural state of things. Xanatos, even if things were to take a horrible turn and he was to be reduced to being a bum in the street, has too much arrogance about him to ever be Charlie Brown.