Heavy
Beowulf Kadmus (Final Fantasy Tactics) vs Georg Prime (Suikoden V) - I guess it's possible if you use purely defender's properties for Georg to avoid a turn 1 status (since it seems there's some debate on whether or not S5's status rates are reduced by MDEF). However, I stick mostly with the attacker's definition/properties of the attacks, especially in cases where its fuzzy. So yeah, Beo equips for HP, survives a hit and whatever he uses is Turn 1 because Georg MDEF is amazingly awful. Georg would need like a 67% crit rate or something in order to win, which I don't think he has?
Light
Ricardo Gomez (Shadow Hearts: From the New World) vs Igrene (Fire Emblem: The Sealed Sword) - Dhyer math prevails part 2.
EDIT: Oh right Pools
H/G: Rupert, Lenneth, Beowulf, Georg
Immediate thoughts: Neither Rupert or Lenneth can take advantage of Georg's awful MDef. He's in his element against both, especially since his own evade is quite strong. Similar to Orlandu, Beowulf may be able to use the same strategy against Rupert with Aspil. However, I'm not 100% sure if he can pull this off as even if he does the same set up, he doesn't have the Auto-Haste and Rupert is fast. However, since his actual damage doesn't matter, he can set up for tanking which may give him enough time to drain all of Rupert's resources? Not sure. Lenneth wants to swap forms against multiple people here. She wants VP1 likely against Beo and Rupert as VP2 doesn't have the same damage output and she really wants to kill both with a OHKO (Rupert to avoid his limit and Beowulf to avoid giving him more status chances). Think she succeeds on Beo. Rupert...not 100% sure where I see his HP. But pretty sure she can manage? Kneejerk is that Lenneth > Georg > Rupert > Beowulf.
M/H: Rudy, Gangrel, Cecilia (ACF), Mog
Immediate thoughts: Rudy one shots Gangrel probably with Lock On SNIPE BULLET. The speed boost might let him avoid a double and Gangrel's P.dur is just so awful. He hits the right defense on Mog and Cecilia...not sure. If she can survive a double attack, she will probably run him out of charges. Even if not, Gangrel's at risk of biting it to a strong Elemental summon due to his awful durability. He's like a variant of Scythe, but avoids initiative issues. Probably beats Mog and that's it. Cecilia runs Rudy out of good damage is my kneejerk and has Quick to give her a boost/Retaliate to wall his damage. Feels like the odds are in her favor. Against Mog, she wins the stallfest and can cast Castle Wall to avoid status issues. Mog against Rudy is a lawlfest and he walls him. Kneejerk Cecilia > Mog = Rudy > Gangrel
L/M: Seifer, Clive, Nowi, Ricardo, Igrene
Immediate thoughts: Oh boy. Seifer's the real anomaly of this pack since how you scale him has a big impact. Regardless though, think Clive sweeps everyone but Nowi who can tank his damage and the counters add up. His excellent accuracy and good durability otherwise shuts down the other three. Nowi sweeps everyone since I don't think Ricardo's damage is enough to punch out her durability. It's close though since she's not particularly damaging either and his regen actually matters here by staving off turns he needs to heal which could run him out of SP. Pretty sure I just treat Seifer as some variant on PC and again, I don't take No Mercy literally. This means he probably loses to everyone sans Igrene since I don't think I see limits as counterable. Nowi > Clive > Ricardo > Seifer > Igrene.
Data Mine
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The Legend of Heroes: Trails of Cold Steel is the only one on that list for me. So...