Edelgard von Hresvelg (Fire Emblem: Three Houses) vs Chris Lightfellow (Suikoden III)
While Chris's defense is pretty nutty and spoils Brave Axe well. I'm inclined to allow the universal combat arts, so the question is does Helm Splitter hit weakness here?! Spamming Silver Axe+ Helm Splitter should be a heal lock with the threat of Raging Storm -> another Helm Splitter if it does. (Although I guess there are scenes where Chris is on a horse, so maybe she's actually a dismounted cavalier not an armor knight!!1!)
Baramos (Dragon Quest III) vs Luca Blight (Suikoden II)
I'm a DQ3 NES voter. Checking, Baramos has 900 HP in the NES version, but very good regeneration (~100 HP a round). The DQ3 NES topic has the endgame damage average being ~130 excluding Goof-Off; call that 115 for a little earlier in the game, and you have Baramos at 0.8 PCHP or so "naively". That's not really enough even with good defenses.
Heavy
Rolf Landale (Phantasy Star II) vs Angelo (Dragon Quest VIII)
No vote, but surely some nasty status.
Claude von Riegen (Fire Emblem: Three Houses) vs Fujin (Final Fantasy VIII)
I'm not sure where I see Fujin's HP, but it's way south of Fallen Star + Failnaught counterattack + Brave Bow attack. And probably only needs to be south of all that + another Brave Bow hit & counter.
Ryuji Sakamoto (Persona 5) vs Hugo (Suikoden III)
So is "Wind of Sleep" (which deals no damage, just a status effect) Wind in Persona-ese, or Ailment? Or both? Ryuji has Evade Wind but also a Wind Weakness, so once this hits he's in trouble. I'm not sure I even want to consider gun status anymore, but even if I did I'd let Yellow Scarf mess with Shock strategies. I'm not sure Ryuji is happy at all, since his damage is killing himself and dealing with Hugo's good evasion and he needs a OHKO I don't think he has thanks to Hugo having healing and it's awful.
Elize Lutus (Tales of Xillia) vs Maya Schroedinger (Wild ARMs 3)
I can technically vote this, but ????.
Middle
Cyrus Albright (Octopath Traveler) vs Messam Elmdore (Final Fantasy Tactics)
Obligatory boo, hiss goes here. Blood Suck.
Lysithea von Ordelia (Fire Emblem: Three Houses) vs Clarine (Fire Emblem: Sealed Sword)
What a wacky match.
Lysithea is +10 Avg. Speed or so when unencumbered but realistically +5-6 Avg. Spd, Clarine is +6 Avg. Spd (and she speed-caps by L15, so it doesn't actually matter whether you use her L15 or L20 figures). So no doubling hype (aside from with an Iron Sword or something weird). Anyway, kneejerk is that Clarine only barely breaks Lysithea's Renewal when not getting Thunder critz, so Lysithea wins, right? But Lysithea is hitting the wrong defensive stat and Levin Sword+ (for counter-attacks) is more than 20 Hit beneath average vs. Clarine's great dodge rate, so she's stuck spamming Soulblade if she wants to stand a chance of hitting. 0.37 PCHP damage vs. 1.38 MDur = 4 Soulblades need to land (maaaaybe 3 if Crest of Gloucster kicks in twice), which means attempting ~8-10 or so Soublades, so breaking an entire Silver Sword+ on this fight. I don't think this is viable because it means triggering Clarine's counters and eventually dying to Clarine damage when she can both attack and counter. Okay, so can Lysithea just go for the total turtle strat of only poking once every 20 turns or so then, right, while occasionally landing a Levin Sword+ counterattack? I... think that when Lys is not triggering counters, Clarine will not be able to slowly overcome Lysithea's regen. Lysithea packs 0.8 MDur (and regens 0.16 Mdur a round), and the lower-leveled no-Elfire version of Clarine deals 0.20 a round - but when taking into account Lysithea's evade, Clarine isn't really winning. That said. Clarine will level-up faster than Lysithea will, and maybe that by the time she hits L20 + C-Rank (her tomes are a lot cheaper than Levin Sword+ / Silver Sword+, too), she can overwhelm Lysithea's regen then off better damage and Hit? Yes, we are talking about a match so stalled out that "level-up a lot" is a legitimate strategy. Or alternatively "break Lysithea's invisible battalion" if we presume that everybody has hidden battalions and eat a stat cost when they retreat despite not being rewarded for them in the stat topic.
Anyway, there you have it - either Lysithea attacks once every 30 turns while regen'ing a lot to slooowly and inaccurately chip her way to victory, or Clarine levels-up and eventually uses Thunder critz & level-ups to smash through Lysithea.
EDIT: Inclined to buy Clarine, think the balance of interps is headed her way - more skill levels, or punishing Renewal by having some sort of Battalion retreat mechanic for very slow fights, all helps spoil a "do nothing with a Levin Sword+ equipped" strategy for Lysithea, and I think Lysithea conclusively loses if she just YOLO spams Soulblade into counterattacks.
Xander (Fire Emblem Fates) vs Nergal (Fire Emblem: Blazing Sword)
This is one of those matches where Xander wants form-choice and regrets being changed from a high-Res Paladin to a Great Knight. Humiliation. (Although... since Tomes are Red in Fates... maybe Lance Xander has a plan to stand next to Nergal, barely not get OHKO'd thanks to blue color advantage, then strike back for a 2HKO? Maybe?)
EDIT: Per Random, Chivalry should tip this to Xander definitely surviving then 2HKO'ing back, using a Lance as well if need be for the first hit.
Light
Primrose Azelhart (Octopath Traveler) vs Lucia (Shadow Hearts Covenant)
Hmm, Lucia's dark resist does make this interesting.