Godlike
Kyogre (PKMN) vs Johnny Garland (SH3): Monkey and I mathed this out in chat about a week ago or so. Johnny can only win this if he goes first, you allow him two Ether Purges, *AND* you don't factor Ether Purge into the average (or assume the current average, instead of 2 Ether Purges + A physical.) Not a great combo for Johnny.
Terra Branford (FF6) vs TimeLord (Saga): Terra can win this if you don't allow Fusion (or by extension, Fusion skills since that's where TL's damage source (Read: Griffith Scratch) comes from) or see her evading enough hits to survive the Overdrive combo. Neither of these are unreasonable, but I allow Fusions and I think it was stated that normal evasion but not blocking, which FF6 does actually distinguish (Blocking = Golem/Interceptor to me) is ignored in Overdrive, so yeah.
Royce (Lunar1) vs Jessica Albert (DQ8): Firebird claims another victim.
Cloud of Darkness (FF3) vs Empyrea (DQ8): HP Difference is a bit too drastic here, considering CoD gets around Empyrea's defenses.
Heavy
Riou (S2) vs Lilka Eleniak (WA2): Lilka can't do enough damage to stop Forgiver Sign from just mudering her.
Crono (CT) Vs Neifirst (PS2): Kneejerk; Crono's not good at taking down bosses, frankly, and while Neifirst had lowish defense, Crono can only take advantage of that by sacrificing a lot of speed, which probably kills his speed advantage as Neifirst was fast.
Nicholai Conrad (SH2) vs Georg Prime (Suikos): PC that deals damage should be able to blitz Nicolai, is my thought.
Zidane Tribal (FF9) vs Grahf (XG): Nice run Zidane, but you just ran into a boss that isn't reliant on elemental damage.
Middle
Gadwin (G1) vs Oscar (FE9): Yeah, definitely remember Gadwin's damage being unimpressive myself by the end of things.
Midboss (Dis2) vs Boyd (FE9): hmm...good fight, unsure who wins offhand though. Its a decent slugfest nonetheless!
Jeane (Suikos) vs Beowulf Kadmus (FFT): Was about to vote Beowulf based on White Robe > Lightning Magic, until I remembered Beowulf has issues just hitting Jeane with status too, to the point where he may be better off just trying to kill her with damage. Jeane may still 2HKO through White Robe though...but then I remembered Aegis Shield exists, which should buy Beowulf another turn, and I believe he's going first. Her raw physical durability should give him a 3HKO to her, I wanna say, and she 3 turns him in response, and I wanna say she's slower.
Shion Uzuki (XSs) vs Anastasia Romanov (SH2): Status I guess.
Light
Jet Enduro (WA3) vs Nana (G1): Gonna go with WA3 PCs > G1 bosses for now or something.
Reis Dular (FFT) vs Soren (FE9): Dragon Reis is a magic tank, I think having a physical is enough to beat Soren?
Chidori Yoshino (P3) vs Rude (FF7): Can't vote.
Miranda (G3) vs Aeris Gainsborough (FF7): I...think Aeris' damage sucks too much even without WOW! given her healing is practically OPB given it heals her less than the amount of damage she receives, and she can't really take much advantage of Seal Evil.