Godlike
Reicher Wallach (Mana Khemia 2: Fall of Alchemy) vs Rean Schwarzer (The Legend of Heroes: Trails of Cold Steel II) - Reicher can definitely tank through a Valimar assault, so Rean's main chance here is opt for Delaying. Problem is, I'm pretty sure Reicher has Delay resistance (it's pretty hard to push him back) and as noted by Random, Rean really doesn't like Remote Mines. If he had more evade, maybe. As is though, I doubt Rean manages to get a big enough Delay number to stop Reicher from getting a turn.
Heavy
Tana (Fire Emblem: Sacred Stones) vs Leo (Fire Emblem Fates) - Tana kinda counters Leo's build.
Yuffie Kisaragi (Final Fantasy VII) vs Rita Mordio (Tales of Vesperia) - If nothing else, Yuffie is faster and definitely 2HKOs. Rita has to worry about dodging a limit too. Even a L1 Clear Tranquil is bad.
Middle
Crono (Chrono Trigger) vs Mirdyn Walhorn (Tactics Ogre: Let Us Cling Together) - Pretty sure NEB's right. Mirdyn gets 4-3'd so Crono overwhelms on a double by casting Lightning 2 twice.
Bowser (Super Mario RPG: Legend of the Seven Stars) vs Nightburn Acklund (Wild ARMs 5) - Nightburn is faster. I think I do see Fear working here (since Nightburn gets hit by stat downs in his game), but I think losing turn 1 is too much here.
Chloe Hertzog (Mana Khemia 2: Fall of Alchemy) vs Shulk (Xenoblade Chronicles) - Unless you allow Chloe the ID weapon, she has no way to bust pass Shulk's limit. Given the fact that Shulk has a couple of ways here to shut Chloe down from doing any damage at all (Monado Shield reduces unique skill damage to 1 and Armor cuts all damage by 75% - which means she's a sitting duck during this time), she has to actually be able to survive a Shulk attack string and I'm not sure about that. Chloe has no way to heal, has bad P.dur and even assuming she can survive one, Glorious Future instantly fills up Shulk's meter. So unless you see Chloe doubling at some point it's possible she just puts Shulk back into another limit, meaning he just wins through defensive stalling. Blame MK2 base physicals being awful for this one.
Light
Miriel (Fire Emblem Awakening) vs Otome Yanagiya (Shin Megami Tensei: Devil Survivor 2) - I was all set to vote Miriel, but then got reminded Dances are AoE and avoid counters. Whoops. And yeah, minor speed below average should prevent a doubling which is all Miriel has if she hopes to win.