Godlike
Riou (Suikoden II) vs Cloud of Darkness (Final Fantasy III): Tank a Forgiver Sign -> Bad Breath.
Isolde Schelling (Mana Khemia: Alchemists of Al-Revis) vs Cidolfas Orlandu (Final Fantasy Tactics): Cid wins if he both 3-2's and 3HKOs, but the 3-2 seems like something he'll just miss. Otherwise... he doesn't 2HKO Isolde so he needs to get two turns in a row or face Bunker Pillar. He can do that, but needs to Night Sword in the meantime. Thing is, I think Night Sword costs him a 3HKO? Maybe not if he equips for power... but then he doesn't 3-2. I dunno, this seems close but leaning Isolde.
Heavy
Purim (Secret of Mana) vs Celes Chere (Final Fantasy VI): Speed's a coinflip (Celes is marginally above if you assume Bard Hat defaults, marginally below if you assume Circlets), so going with the one who has MBlock in this status-off.
Middle
Cleo (Suikoden) vs Tharja (Fire Emblem Awakening): Cleo definitely wants to go for basic physicals here, fire magic both misses a lot and makes Tharja's Waste hit reliably. That said, even if she doubles Tharja (which... she probably does, she is fast), she only 4HKOs so that gives Tharja three attacks. And... due to accuracy and Cleo's magic durability, she doesn't actually 3HKO. Only hope is to go for Nosferatu, and that does eat into Cleo's damage pretty notably. And... yeah that reduces Cleo's damage to an effective 8HKO or so, before factoring in Tharja's miss rate or Vengeance, which isn't good enough.
Karsh (Chrono Cross) vs White Rose (SaGa Frontier): LightSword both gives White Rose a 2HKO and enough evade to reliably dodge a Karsh turn.
Light
Saleh (Fire Emblem: Sacred Stones) vs Mustadio Bunansa (Final Fantasy Tactics): Slayer of Eirika route PCs, Mustadio once again doubles and that pushes his damage to 3RKO while avoiding counters, Saleh doesn't 2HKO back.
Tricia (Soul Nomad & The World Eaters) vs Soren (Fire Emblem Series): Mage matchups.