Godlike
Yurika Misamaru (Super Robot Taisen Series) v Fou-lu (Breath of Fire IV) - SRW~
Reicher (Mana Khemia 2: Fall of Alchemy) v Zophar (Lunar: Eternal Blue Complete) - Letting Reicher inflict Break seems fair. It's less of a status effect and more of an accrued effect from Reicher's piled-on damage, and I don't think I'd let standard boss immunity block this? (Actually, I have no idea how Break works in MK2, but if it's like MK1, then I think this is how I'd vote.)
Taupy Toplan (Sands of Destruction) v Myria (Breath of Fire Series) - Not a bad fight, but the healing off of that speed outpaces Myria's magic damage.
Adramelk (Laggy Fantasy Tactics) v Xorn (Grandia III) - LFT~
Heavy
Domon Kasshu (Super Robot Taisen Series) v Weltall 2 (Xenogears) - SRW~
Puniyo (Mana Khemia 2: Fall of Alchemy) v Zed (Wild ARMs) - Kneejerk
Viese Blanchimont (Atelier Iris: The Azoth of Destiny) v Cathedral (Xenosaga: Jenseits von Gut und Bose) - anti-Cathedral vote~
Ghost Ship (Etrian Odyssey III: The Drowned City) v Arnaud G. Vasquez (Wild ARMs 4) - EO~
Middle
Lilina (Fire Emblem: Sword of Seals) v Riki (SaGa Frontier) - What is Riki doing in Middle with an 8HKO? Inflict Charm, profit. Lilina wishes FE6 Thunder had an innate damage bonus to Dragons~
Lilianne Valendorf (Mana Khemia: Fall of Alchemy) v Lilly Pendragon (Suikoden III) - I imagine this being a literal slapfight, and it is hot.
Cornet Espoir (Rhapsody: A Musical Adventure) v Yosuke Hanamura (Persona 4) - Eat Syrupy doom, Brosuke!
Luso (Final Fantasy Tactics Series) v Ramza Beolve (Final Fantasy Tactics) - Speed Rend -> Win. Soldier isn't every PC's default class, it's just Luso's, so it works for me.
Light
Cheripha (Valkyrie Profile: Covenant of the Plume) v Beautifly (Pokémon) - She immunes Paralysis, can use the Blue Gale to get rid of the Earth-typing on her physical, and she gets counters. It -might- take a while to finish off Beautifly if you don't see her SC as OHKOing through the healing, but the healing is only 50% and it has limited uses of that.
Bibarel (Pokémon) v Vinsfeld Rhadamanthus (Wild ARMs 2) - Defense Curl->Roll Out strategy on Vinnie?! I'm for it.
Lassi (Magical Starsign) v Kahn (Breath of Fire IV) - The MP Regen means she can heal forever and she's much much faster than Kahn. The eventual Planet Alignment bonus should be plenty to put her in range to finish him off on a double.
Saki (Luminous Arc) v Kain Highwind (Final Fantasy IV) - JUMP DOWN VS. KAIN! OF COURSE!