Godlike
Yaridovich (Super Mario RPG: Legend of the Seven Stars) vs Athos (Fire Emblem: Blazing Sword): His ridiculous MDef ruins Athos' drain game, so he should be able to overwhelm it. He 2HKOs even if you assume half-timed defence (which I do... most of the time at least) and doubles against Nos, so yeah that should be enough. If only Athos' ITD tome was lightning...
Ryu (Breath of Fire IV) vs Yunalesca (Final Fantasy X): Absorb hacks the dragon forms to pieces pretty badly (as it does aeons in-game). If Ryu somehow makes it to form 3 there are many, many problems waiting there.
Orlouge (SaGa Frontier) vs Fou-lu (Breath of Fire IV): Uhhh... they have similar HP and stuff. Fou-Lu is faster (except than Orlouge's angel attacks, but those are all physical or wind, so wind mode tyrant says nope). Fou-Lu uses Dark Wave immediately, does a crapton of damage. Orlouge responds with Triple Salamander, which also does loads of damage. Fou-Lu... should be able to kill in two more turns, though; two physicals should be enough, especially since Orlouge is slightly vulnerable to ITD.
Heavy
Kiryl (Dragon Quest IV: Chapters of the Chosen) vs Peter (Shining Force II): Kinda shows how Peter is a bit out of his depth in Heavy.
Oerba Yun Fang (Final Fantasy XIII) vs Wakka (Final Fantasy X): I'm pretty okay with hyping Fang shortening her chain a bit in this case, sure... but she absolutely has to land Pain turn 1, and Wakka will equip for blind (read: Pain) resistance. Meanwhile, there's zilch she can do about Sleep Buster.
Yuffie Kisaragi (Final Fantasy VII) vs Angela (Seiken Densetsu 3): Snowman is "can't act" so yeah it is kind of a win here. I would be willing to see it as equivalent to Stop... but that turns out to be one of the only statuses FF7 can't actually block.
Shadow (Final Fantasy VI) vs Dart (Legend of Dragoon): Hmm I think these days I'm willing to vote on 200 initial SP. So Dart isn't quite a free win as he gets a powerful 2HKO and a durability push between his first and second turns. That said, he just misses the OHKO on Shadow, who 2HKOs him first with ITD weakness-hitting Ice Brand throws.
Middle
Henry (Fire Emblem: Awakening) vs Clarine (Fire Emblem: Binding Blade): Tomebreaker is definitely difficult here. Clarine's res apparently isn't that super-high anyway.
Spherimorph (Final Fantasy X) vs Hippopressor (Mega Man X: Command Mission): I do think Spherimorph can OHKO shark missiles due to their bad defences but... he also faces their evasion, so most of the time it won't work. So yeah, ITD damage does its thing.
Mishaela (Shining Force) vs Miranda (Grandia III): Something about hyping Tremor feels seriously off to me, but yeah Mishaela's durability is pretty wretched and she could be seen as having last strike so maybe...
Light
Rahal (Suikoden V) vs Red Wizard (Final Fantasy): Not that I agree with RW being a Middle, but Rahal... is bad.
Rude (Final Fantasy VII) vs Blissey (Pokémon): Uhhh I dunno. You need to do 43% damage to kill Blissey, assuming you go first. Does Rude do this? Possibly! Of course, Rude might also be slower than Blissey. ... actually he almost certainly is, Gen 2 speed average being low is a help there. Okay then.