Godlike:
Altima (FFT) vs Rabbid Luigi (Mario Rabbids 1):This doesn't seem that close? Petrify/frog/sleep all win the match instantly, that's turn 2 for Grand Cross at worst. Even slow/berserk are pretty devastating, so arguably we're talking turn 1. But even at turn 2, and even nulling it every other turn, RL damage isn't outracing that.
Rhea (FE:TH) vs Sephiroth (FF7): Not a huge amount of respect for Rhea against multitarget. One use of Deen blows up all the barriers at once, Rhea loses a turn to stun, and then Sephiroth probably kills her in two more attacks.
Heavy:
Claude (TH) vs Margulis (XS2): This is a shockingly easy matchup for Claude. Piercing physicals are Margulis's bane (he only has 1.8 PCHP against them or so, is this still Xenosaga 2?), and I doubt Margulis's 122% speed is enough to keep Claude from quadding him. Toss a Fallen Star in and Claude is taking two hits during this fight at most.
Rubino (Brig) vs Saki (SH2): 2HKOs with Fall Berg, can survive Energy Charge, is immune to Seal. Great matchup for Rubino.
Fujin (FF8) vs Kain (TAY): Fujin is squishy but not "dies to averagish damage" squishy. Blind and confuse are both deadly here, and Kain can't block both.
Hendrik (DQ11) vs Rei (BoF3): Hendrik reduces Death to turn 5-6 or so (depending on how death resistance accessories stack) but it still lands before Hendrik's third turn, and I don't think he can 2HKO? Open to arguments.
Middle:
Cyrus (OT) vs Leo (Lunar:EBC): Definitely kneejerk Cyrus as the faster one on the grounds the Octopath speed barely matters. Still... think Leo might have this. Cyrus's best strategy is to use Fire Storm, Fire Storm, 3 BP Fire Storm (or similar). This is a lot of damage... except the final attack is "only" about PCHP (i.e. Leo lives) and the first two are about a quarter of PCHP, so Leo just heals them off with Soul Blade. Leo has about 1.1 mdur, so with Soul Blade's healing him twice that rises to ~1.54, and Cyrus only does 152% magic damage total. Close.
Oengus (CoL) vs Amarant (FF9): The creeping chances of death and turn knockback (the latter just wards off any doubles, granted) mean Amarant can't win a super-long fight, and a quick win is also out against Oengus pdur.
Dorothea (FETH) vs Tiamat (FF1): They're in opposite sides of Middle, but everything about this match lines up to favour Dorothea (her mdur, Tiamat's non-elemental mdur). Tiamat wins on turn 4 (43% damage, but Dorothea regens 20% after each one). Dorothea kills with three Hexblades.
Light:
Talia (Brig) vs Cecil (FF4)
Difficult fight, but the result is actually quite clear. Talia does 35% with Heavenly Sacrifice (can use 20 times) and heals 12%, at base. Cecil pdur makes this 22% damage and 9.5% healing. Meanwhile, Cecil does 27% to average which is 22% to Talia. Talia counters for 21%. Cecil can heal for 26% of his HP, 25 times. Talia goes first but I figure they never double each other thereafter.
If Talia is uninjured she's using her basic physical to 5HKO. If Cecil tries to stick damage she drains instead, and there's no way Cecil can kill her until she runs out of MP (i.e. she uses the draining attack 20 times). Cecil can try to gain momentum by healing, which DOES outpace Talia's damage... except that this is lost whenever he attacks himself, because Talia counters him. I'm just not seeing where Cecil makes any meaningful headway to start cutting through Talia's MP.
Malak (FFT) vs Hubert (FE:TH): SUPER WHY. Hubert damage is just going to be utterly anemic here.
Umaro (FF6) vs Flayn (FE:TH): oh god. Okay, so, by my calculations, Flayn BARELY avoids being doubled if she equips Wind + Caduceus. And... that's the fight, really. Umaro should do high 3HKO but Flayn's 50% regen offsets that. If she were being doubled, Umaro would take this for sure.