Royce (Lunar1) vs. Cloud of Darkness (FF3) - Cloud vs. Empyrea was actually extremely close, due to Empyrea being able to Zap / physical out the tentacles reasonably quickly. I still voted Cloud due to the Particle Beams toward the end. Royce, so far as I recall, doesn't have much (good?) MT, so she's not dispensing with the tentacles fast enough to keep Cloud's damage output under control.
Heavy
Riou (S2) vs. Crono (CT) - Go die Suiko2 and your recruitment. Sadly I suspect that Riou generally wins even without Forgiver Sign - beat up Crono, heal the second Luminaire off, potentially go berserk and finish the job, has a second shot of good healing even if he didn't go berserk.
Georg Prime (Suikos) vs. Grahf (XG) - Actually fairly close. Not sure, though leaning Georg.
Middle
Oscar (FE9) vs. Boyd (FE9) - Yay for tossing out DL scaling and being able to go on in-game comparison.
Beowulf Kadmus (FFT) vs. Anastasia Romanov (SH2) - Beowulf is slow (no Thief hat). Ana HP-1s him, and a lot of Beowulf's tricks now don't work in time.
Light
Jet Enduro (WA3) vs. Soren (FE9) - Hey, wait a second here. Jet was no Gallows, but he wasn't Clive either. He's not that accurate, and he has game-worst magic resistance. I don't see why people think he wouldn't get countered either, he certainly will. Then again... checking the stat topic, Soren's speed is a lot less than I expect (maybe I got lucky in my playthrough? He consistently doubled everyone there and had a good ~26 or so Speed, IIRC). So. Jet shoots Soren. Soren counters, then Soren hits Jet again. Jet.... is probably on death's door at this point, so Gatlings, and probably has more than 50 FP (if he's at least level 44, which should be easy). That's three hits from Jet, and even if one missed, that's probably game. Still! This is pretty close. I can even see Soren perhaps 2HKOing here, which might flip things.
Rude (FF7) vs. Miranda (G3) - Rude.
Re upgrades: Meliadoul's breaking is a lot less relevant than usual due to the fact she's going to have to break 4 different weapons before it puts an FE9 character out of business. That said if you only allow super-forged weapons but only one per character, I suppose it can put a kink in their damage. Anyway, I think she still wins, but due to the Protect on Save the Queen and avoiding counters with Mighty Sword, not the actual equipment breaking itself.