Cecilia Lynn Adlehyde (Wild ARMs) vs Naja (Sands of Destruction)
Can't recall if SoD characters could equip 2 accessories or 1. Anyway, it's an interesting match mostly based on Prison hype for Cecilia, since if Naja can only equip 1 accessory, then he either blocks ID (and rolls to Cecilia's other status options) or everything-but-ID. However, Naja has Cleansing Cry, which coinflippy beats Prison? Similar to whether something like a DQ8 Wave of Ice stops Air Anchor I guess. What turns it to me is that even if Prison hype is go, it can miss, and further Naja has a strategy that might get him through anyway - come into battle with lots of morale and spam his 60% Stun (basically turn skip) Strike move until it hits, then resume Flurry Chains / buffs for damage. Which will include his AGI booster. This kind of nukes his DL damage, but he has an unreliable lockdown with this strategy, and Cecilia's durability isn't great, so he's still got a shot before Cecilia gets unlucky on resisting the stuns.
Chaos (Final Fantasy) vs Cid Raines (Final Fantasy XIII)
Ew Cid part II. His durability is less stupid, sure, but stupid enough, and Chaos is not actually good anyway.
Millenia (Grandia II) vs Umi (Cthulhu Saves the World)
I can theoretically vote on earlygame Umi. Maybe later.
Tengaar (Suikoden Series) vs Raynie (Radiant Historia)
Even if Revenge Earth > Sleep Break, Raynie might go first anyway.
Edit: Tengaar speed hype? Sure I guess.
Brad Evans (Wild ARMs 2) vs Sazh Katzroy (Final Fantasy XIII)
Sazh has a 2HKO post buffs IIRC, so a 3HKO to Brad. He opens Haste / Protect, spends half a turn on Bravery, then spams attack, so 4.5 turns or so. Fight hinges on whether you let Brad get the Courage Rune the stat topic gives him which raises his speed from "game worst" to "above average," and be darned if I can remember if this is merited or not. Anyway, with the speed boost, I think Brad wins - he opens with a Lock-On ARMS before Protect goes up and Sazh is too far behind. Slow Brad only gets 3 turns against a Protected Sazh, and don't think he can break him, though it's close. I'll vote for Sazh though it can go either way.