Godlike
Indalecio (Star Ocean: The Second Story) vs Nailah (Fire Emblem: Radiant Dawn): Headache, depends on a few things. One is Nailah's evade; with the authority boost it's over 50% and thus she should be in good shape regardless. Without, it's a bit more trouble. Another is exactly how Indalecio's turns come. I'm not sure who goes first here, even - both are notably mobile in their home games. Indalecio badly wants to both get the first turn and get another turn immediately after Time of Truth kicks in. Otherwise... pretty sure I see Indalecio being three-rounded here (he's in much better shape if it's four), and needs at the very least one high-HP spell plus one Explode to win. I'm not certain. Trying hard to avoid just voting for the obvious bias choice here. EDIT: The more I think about it the more I really doubt Indalecio has time to use both Time of Truth and charge Explode before Nailah gets another turn, which makes this pretty hopeless especially since he needs some other judgement calls to get that far, to me.
Tibarn (Fire Emblem Series) vs Cloud of Darkness (Final Fantasy III): Tibarn can win, but he needs to avoid Bad Breath. To do this you pretty much need to see Bad Breath as evadable via evade and not as a pure status move... but since pure status moves hit through Pavise and evade and only hit Res (and Tibarn's isn't actually good), that's a tough argument to make. It doesn't help that, without Tear, Tibarn needs three turns to kill here.
Lucina (Fire Emblem: Awakening) vs Reclaimer Dragon (Wild ARMs 4): Well Reclaimer Dragon won't be doubled. If it can hit twice through Lucina's evasion (or if its attacks don't trigger counters), then it should outslug, as I think it's just durable enough to tank a Lucina turn. Abstain until I hunt down Tide and figure out the answer to those questions. <_< EDIT: All moot because if it can tank a turn, it can just spam sleep. And I'm pretty sure it can.
Hortensia (Breath of Fire: Dragon Quarter) vs Lenneth Valkyrie (Valkyrie Profile Series): Lenneth does 1.6PCHP, which... I figure is probably enough to kill Hortensia, even with her pdur and absolute defence? It is by the endgame damage figures. Granted, those might be too high for when you fight Hortensia... but I'm not terribly inclined to make judgement calls for regents like that. Could be argued.
Heavy
Hugo (Suikoden III) vs Athos (Fire Emblem: The Blazing Sword): Nosferatu wards off Hugo's hopes here even if he manages to 2HKO + double.
Beowulf Kadmus (Final Fantasy Tactics) vs Marle (Chrono Trigger): Break should still work through Vigil Hat (they don't stop ID) and still be turn 2. Marle is faster and has status of her own, though. Beowulf should probably block confuse and then pray his shield can protect him from Stop? That should be 30%, while Break is 41% but the first chance kicks in after Marle's... which *runs some calculations* gives Marle a 51-49 advantage in odds to win (actually sliiightly higher because Beowulf can run out of MP, though not often if he equips for it). Alternatively, Beowulf blocks stop instead, which leaves him vulnerable to Provoke. That leaves an open question of what type of attack Provoke is (it's not starred as magic, and isn't affected by any stats in-game) but eh either it's affected by Beowulf's faith and hits his better shield and isn't, and those probably about balance out. Marle is now clearly favoured, but she'll have to land confuse repeatedly in her lockdown? One confuse does let her haste and have a ridiculously big advantage, though, since she can wait for Beowulf to whiff then get three attacks in a row. And if you let her switch bows after Beowulf decides his statusblocker (I... probably do, you can change equipment more often in CT than you can in FFT), then she'll slow him as well. And of course there's an argument that Provoke doesn't hit any evades at all. Think that's that. Really close though, as per the Break vs. Stop notes above! (Way less close if you see Vigil Hats stopping break.)
Tana (Fire Emblem: The Sacred Stones) vs Alfina (Grandia III): Gut vote, could be argued. Alfina could lock Tana down forever but with her evade that seems difficult. EDIT: Fast Stun Force changes everything.
Razelux Meitzen (Mana Khemia 2: Fall of Alchemy) vs Arnaud G. Vasquez (Wild ARMs 4): Raze is entirely evadable.
Middle
Yulie Ahtreide (Wild ARMs 4) vs Bowman Jean (Star Ocean: The Second Story): Bowman has 1.6x average damage = 64% = 97% to Yulie. That's assuming I don't antihype Sakura Attack's speed and see it going second.
Chisato Madison (Star Ocean: The Second Story) vs Nowi (Fire Emblem: Awakening): Best-case scenario for Chisato is that she both doubles and 6HKOs... but that still gives Nowi way too many turns.
Chloe Hurtzog (Mana Khemia 2: Fall of Alchemy) vs Guy (Lufia II: Rise of the Sinistrals): EDIT: Trusting people here. If Guy's arguments rely on starting IP which I don't give, or seeing SDs lower than I do, then I think Chloe definitely has this for me.
Sara (Breath of Fire) vs Bowser (Super Mario RPG: Legend of the Seven Stars): Bowser has serious trouble winning this even if he goes first and Fear is effective. And there's not really a compelling reason to see the latter in particular.
Light
Jane Maxwell (Wild ARMs: Alter Code F) vs Miriel (Fire Emblem: Awakening): Jane respect not found. I guess she can play guessing games with her evade-and-counter move, but this still gets her outslugged pretty badly assuming each guesses right 50% of the time (not to mention Miriel can turtle while she runs out of MP).
Big Joe (Xenogears) vs Sacred Slayer (Wild ARMs XF): Isn't Big Joe.
Ward Zabac (Final Fantasy VIII) vs Miranda (Grandia III): Probably can get around a limit with a timely use of Wow.