Godlike
Chaos (FF1) vs. Chaz Ashley (PS4): Need to look a few things up. Thinking Chaz has a good chance with 2 Reflect Shields to lower the ID rate (proven to hit magic defense in game), and then nailing Chaos' low HP, and goes first.
Velna (LoL2) vs. Kurando Inugami (SH2): Need to look Velna up again.
Killer (SH3) vs. Yunalesca (FFX): Yeah, durability difference works for me.
Lamington (Dis) vs. Jade (BoF1): Jade is Lamington but better at like...everything. And even hits Lamington's lower defensive stat.
Heavy
Justin (G1) vs. Decus (SO2): This was discussed in chat a bit, I think Decus was proven to have the edge, despite Justin hitting weakness.
Janus Cascade (WA3) vs. Suicune (PKMN): Suicune is a tank with good damage and passable speed. Janus has...uhh...3HKO damage <_<?
Alis Landale (PS1) vs. Hahn Mahlay (PS4): I'd almost buy Rope spam if Hahn didn't have high magic defense.
Ziggy (XS) vs. Rose (LoD): Is getting her 2nd turn with no hindrances, Ziggy can't stop instant deaht.
Middle
Nelis (S5) vs. Saki (G1): Blech, Suikoden 5 is the one game I'm not certain on 90% of its cast how it duels DESPITE playing the game -_-
Aika (SoA) vs. Erk (FE7): Delta Shield owns Erk. Fail.
Meredy (ToE) vs. Pent (FE7): Better.
Huxley Hobbes (VH) vs. Albert Serdio (LoD): Huxley was the priest, right? Don't think he can realistically take down Albert.
Light
Futch (Suikos) vs. Jean (BoF2): Instant Death.
Cius (S5) vs. Euram Barows (S5): Ok, see my comment about S5? Well, I know Cius is your typical Suikoscrub, so that's one thing. But more importantly, I know for a fact that just about everyone in the DL this side of Jogurt > Euram.
Rafa Galthana (FFT) vs. Chongara (AtLC): If nothing else, fuck Chongara.
Rinoa Heartilly (FF8) vs. Fargo (CC): If there's one thing Chrono Cross is good at, its damage manipulation and avoiding Limits. Fargo is no exception in this regard.