Godlike
Rupert Dandridge (Wild ARMs XF) vs Lamington (Disgaea: Hour of Darkness) - Well, technically I haven't played the game, but I have basically co-played it with my roommate and seen all the bosses in action, so I do feel comfortable voting on this. Anyway...mmm...think I'm going for Lammy here? Generally a decent fight, and Maximum Risk is powerful, BUT it is hitting Lammy's physical defense, which is his awesome stat. Don't think I'd see Rupert's water resist hitting Judgment's ice damage, so it still hurts.
Dheginsea (Fire Emblem: Radiant Dawn) vs Xorn (Grandia III) - Mmm...think I'd see Thunderclap as wind? Don't think it matters anyway - Xorn EXAs, nukes with the magic anyway, eventually crushes with the time-bomb minefield of doom.
Persephone (Wild ARMs 5) vs Ted (Suikoden IV) - Persephone. Overkill, survives anything Ted does well enough.
X (Mega Man X: Command Mission) vs Ramirez (Skies of Arcadia) - X. Defends against ID with hyper mode or a status blocker. Ramirez...is still pretty good there, but think he falls off trying to top X Heart.
Heavy
Ragnar Blitz Lebrett (Wild ARMs XF) vs Freyjadour Falenas (Suikoden V) - Ragnar. Decent enough.
Masaru (Live a Live) vs Yuffie (Final Fantasy VII) - Masaru. Yes LaL fun!
Hollander (Crisis Core: Final Fantasy VII) vs Hojo (Final Fantasy VII) - Ok, haven't observed enough CC to vote on this, I think!
Elincia (Fire Emblem: Radiant Dawn) vs Zera Valmar (Grandia II) - Zera. Damn you FE10 Mercy! Alternatively, I think I might actually allow Zera the Valmar Core form, which...slaughters.
Middle
Koromaru (Shin Megami Tensei: Persona 3) vs Blanca (Shadow Hearts: Covenant) - Bleh. I can't even hype Sukukaja here, I think, since Blanca can ignore the evade with Red Comet...granted, that does hurt the MP reserves...
Katina Tarask (Super Robot Taisen Series) vs Ashton Anchors (Star Ocean: The Second Story) - Eh...Katina. Though, TRI-ACE hype might work here!?
Thief (Final Fantasy X-2) vs Gallows Caradine (Wild ARMs 3) - ...wow. Steal Time. Gallows wins outside of that.
Cinnamon (Mega Man X: Command Mission) vs Lemina Ausa (Lunar Eternal Blue Complete) - Cinnamon. I seem to remember that resisting any element resisted Catastrophe. Even if not, Cinnamon just survives and heals it off anyway.
Light
Chidori (Shin Megami Tensei: Persona 3) vs Mel (Suikoden III) - Chidori. Tetrakarn limit phase is not missed!
Puni Punist (Atelier Iris 2: Azoth of Destiny) vs Magikarp (Pokémon) - ...damn. need to play AI2.
Sothe (Fire Emblem: Radiant Dawn) vs Rennac (Fire Emblem: The Sacred Stones) - Sothe. GODLIKE RES WILL NOT SAVE RENNAC NOW. Though...MF6 form? I need to play that form, if it does exist!
Corselia (Suikoden Tactics) vs Reis Dular (Final Fantasy Tactics) - Corselia.