Heavy:
Lassic (PS4) vs Hugo (S3) - Hellfire I can see as killing in...three hits (or two and a physical string. Unfortunately for Hugo, Another Gate is magical and hits high 2HKO. At best, it heal locks. At worst, he tries to brute force the matter and gets outslugged. [EDIT] this is more one-sided than I thought. I forgot that Hugo only gets one shot of Hellfire.
Middle:
Crono (CT) vs Hendrik (DQ11) - Will say that Crono does not like that I hold Hendrik to my TB speed interps, which means his low speed is offset by the fact that as it is TB, it effectively only impacts the first turn. Breaking this down:
Luminaire (20 MP) hits for ~34% of Hendrik's health from raw, so a 3HKO by the barest of margins. As this is Lightning damage, though, Drustan's Shield and Metal King Armor will cut this down to, assuming scaled to 20% resistance, 23.3%, so Crono is ultimately high 5HKOing with magic as long as Hendrik's running the shield. Crono's other damage option for this, Confuse (12 MP), hits for either 22.6% (off of the Swallow) or 27.9% (off of the Rainbow, but sacrificing most of his speed advantage for something that'll ultimately be at a disadvantage), not factoring for deflection. These are his main options. If he's below 12 MP, he can go for Spincut (4 MP, ~12.6% damage on Swallow), but that is an emergency option.
Worth noting that this is already a fairly generous interp of Crono's Swallow-based offense for demonstration purposes; it is reasonable to assume that with DQ's subtractive defense, it would be more negatively impacted.
Hendrik can shore up his defenses even more, however; Buff can reduce Confuse (particularly off the Swallow) to negligible damage for the duration, and one shot of Magic Barrier will halve Luminaire's damage. A second will quarter it. Blockenspiel can halve all damage until Hendrik's next turn, and Healmore cures roughly 29.4%. Lastly, he has a 20% block rate, and I do recall DQXI blocking working on more skills than CT evasion does, so between the number of attacks flying around and this detail, I am willing to lean into this as a clutch factor.
So essentially, Hendrik has two win conditions; either Crono hits 11 or less MP (whereupon he does scratch damage) or he can get three turns to attack Crono (Hendrik's damage is not great. However, he can 3HKO Crono physically. (under the raw average, he has an argument for 2HKOing with how DQXI allows hot-swapping: Gyrfalcon->Unbridled will get him to damn near exact HP kill, but for the purposes of this I'll be taking the harsher 3-turn average)
If Crono's coming in with anything other than the Swallow, he loses. Crono gets first turn, then trades while Hendrik buffs, heals, and beats him down.
With my speed and turn order interp, the following would roughly take:
Crono: Confuse (22.6%) (78/90 MP)
Crono: Confuse (45.2%) (66/90 MP)
Hendrik: Buff. Confuse does scratch damage now.
Crono: Luminaire (68.5%) (46/90 MP)
Hendrik: Healmore (39.1%)
Crono: Luminaire (62.4%) (26/90 MP)
Hendrik: Healmore (33%)
Crono: Luminaire (56.6%) (6/90 MP)
at this point Crono is out of gas and at Hendrik's mercy, or lack thereof.
If we take Crono as straight doubling and going first, we'd have:
Crono: Confuse (22.6%) (78/90 MP)
Crono: Confuse (45.2%) (66/90 MP)
Hendrik: Buff. Confuse does scratch damage now.
Crono: Luminaire (68.5%) (46/90 MP)
Crono: Luminaire (91.8%) (26/90 MP)
Hendrik: Healmore (62.4%)
Crono: Luminaire (85.7%) (6/90 MP)
Still out of gas. Spincut isn't doing anything here through Buff.
Crono straight-up 5-2ing would look closer to:
Crono: Confuse (22.6%) (78/90 MP)
Crono: Confuse (45.2%) (66/90 MP)
Hendrik: Blockenspiel (incoming damage halved)
Crono: Confuse (56.5%) (54/90 MP)
Crono: Confuse (67.8%) (42/90 MP)
Crono: Confuse (79.1%) (30/90 MP) (Blocking may start to trigger around here)
Hendrik: Healmore (49.7%)
Crono: Confuse(72.3%) (18/90 MP)
Crono: Confuse(94.9%) (6/90 MP)
Hendrik: Healmore (65.5%)
Even with this, Crono is going to be completely out of gas and essentially trying to chip Hendrik out, who can beat him to death with impunity. Ultimately, to win, I feel Crono would need: a speed spread that lets him 8-3 Hendrik at minimum, plus the more favorable damage scaling treatment (again, this is a bit of an overshoot for Crono's physicals, as the nature of subtractive defense means he would be likely doing less than demonstrated here with his below-average damage on Confuse), and needing the shield block to never go off across the many, many attacks Hendrik will be facing. With all that in mind, I feel firmly secure in awarding the win on this match to Hendrik. Good damn match.
Hahn Mahlay (PS4) vs Guy (Lufia 2) - Feels fairly straightforward. Guy's going to generally be on the back foot between debuffs, itemcast Deban, an extremely generous TP pool for healing, and the looming threat of ID that lets him win without building up extra IP for Guy.
Light:
Ophilia Clement (Octopath) vs Setzer Gabianni (FF6) ...i've not played OP enough nor remember enough of Setzer to make a good judgment on this one.
Thief(male)(FFT) vs Kain Highwind (FF4) - not sure how much I respect Steal Weapon? I remember you could hot-swap weapons in the SNES-era FFs, but...Kain's damage is utterly miserably bad as-is anyway. ...as is Thief's. Thief is faster, and clearly what we should be hyping is that non-elemental Jump is regarded as Throw-element and thus you have an argument for Catch working against it and...
okay, in seriousness, both are about the same, but I *believe* Thief is faster. I think...hm, Thief probably edges out with status weapons. A slapfight for the ages. One of the greats for sure.