Godlike:
Ghaleon (Lunars) vs Hugo Hewitt (WA4): Assuming a couple Rock'n'Rolls are enough... if they're not Ghaleon could actually lose this which is kind of embarrassing? But probably not. Rock'n'Roll+Chaos Shield ensures the second half of the double isn't wasted. EDIT: I forgot Inferno/Nitro Dagger were MT too, okay never mind this isn't even close.
TimeLord (SaGa) vs Orgulla (XS2): Durability. Ways to get around Glass Shield.
Red Fiend (Lunar:EBC) vs Yuna (FFX): Tapes down the X button on her PS2 controller, goes fishing.
Zophar (Lunar:EBC) vs Reicher (MK2): Either Zophar has multiple parts which really fuck with Reicher's Remote Blade focus game (and does loads of damage really fast), or he gets Fate Storm.
High Heavy:
Chris Lightfellow (S3) vs Lyon (S5): Her SL comes out faster than Lyon's stuff. Although even if this weren't the case, provided Setting Sun isn't turn 1, Chris could just SL in response to that, or heal in response to Vermillion Sky?
Celes Chere (FF6) vs Layna (SN): Status or Vanish.
Lulu (FFX) vs Ryu (BoF2): Oh dear.
Low Heavy
Rune Walsh (PS4) vs Grunzford (SN): Yay!
Aldelbert Steiner (FF9) vs Marle (CT): Stop or Confuse.
Kresnik Ahtreide (WA4) vs Rei (BoF3): Unless Rei could OHKO in Weretiger? Trying to land BoF3 Death against Kresnik MDef is noooope. EDIT: Riiiight, Kresnik's healing isn't that good, so Weretiger beatdown overpowers it easily after Speed.
Middle:
Tear Grants (TotA) vs Roger Huxley (SO3)
Argilla (DDS) vs Ulrika Mulberry (MK2): Argilla may block silence, but Cannon Ball is still very bad news (turn 2 for at least one of Slow/Curse, turn 3 for both). Her only hope is to cause turn 3Panic with Tentarafoo I think (raw damage gets responded to with Healing Reverb)? At least her having healing wards of ItD... until slow or curse lands. So... Cannon Ball, Tent, Cannon Ball. At this point either slow or curse has landed. If it's slow, then Ulrika can ItD with her next turn and win before. If curse... actually she can't stop two more Tentarafoos, so she's best off putting up a healing timed card and/or Elemental Barrier with her third turn, so that she can survive being Panicked? Since Argilla won't be healing during this time, I think Ulrika wins if my memory of Panic's duration is correct (~3 turns). Pretty close, but feels like Ulrika has the edge.
Gaff Gafgarion (FFT) vs Ramza Beoulve (FFT): Feels weird, but not that weird. You have to be clever and monkey with your setup to win the Ramza vs. Gafgarion duel without help from your allies in-game.
Lilina (FE6) vs Tony (WA4): EDIT: Re-thinking things... there are no lightning attacks in WA4, really (at least on the PC side) but Short Circuit very much has a lightning feel to it, and it's a big weakness which I feel should probably be reflected in some way (bosses giving good damage to Jude of the 1.4x average speed is bad news for them). Toss in intuitive arguments for lightning beating mechs and I'm willing to see Lilina hitting weakness here. Subjectivity ahoy, obviously it's reasonable to disagree.
Shame:
Millie (S2) vs Doll (SaGa): There's a possibility these are the two best in this half of the draw? If so that is terrifying.
Alfred Schroedinger (WA3) vs Spiritmaster (BD): I think.
Alenia (S5) vs Jogurt (SF1): Yup.
Rahal (S5) vs Onix (PKMN): Onix has a 2HKO to average with Bind-spam against those who are both slower than him and unimpressively evasive. It doesn't come up that often, but Rahal is special. EDIT: Okay, 3HKO, but a high one. Probably just enough to 2HKO Rahal before he potentially OHKOs back. Yikes, how does this match make it look like both these two have offence.