Using stat topic numbers and my scaling method, Holly's around 1.66x PC HP. For pure curiosity purposes, unscaled, against a 2.5x average damage for PC HP threshold, she has 6.66x PC HP. So, for me, she can patch away up to 48% PC HP in damage per Cure casting.
Holly Whyte vs Palom (FF4) - Palom's actually pretty good at punching past Holly's healing. Her offense, on the other hand, is just too anemic to threaten him. Of course, FF4o Palom likely loses because that durability, jesus.
Holly Whyte vs Jude Maverick (WA4) - Jude's also pretty good at overwhelming the healing with the speed game on Assault Buster. To make matters worse, he halves wind.
Holly Whyte vs Judecca (WA2) - Judecca, on the other hand, struggles even with the borderline 2HKO and is slower. The inaccuracy on Miriam also speaks volumes against him.
Holly Whyte vs Billy Lee Black (XG) - Build up AP, mock the damage with Wind Shield and collect victoly via chipping then doubling at worst. Billy's on a whole other tier compared to Holly.
Holly Whyte vs Solo (DQ4) - I'm fairly sure Solo can pull this off, be it via chipping or possibly even slowly trying to connect his sleep spell.
Holly Whyte vs Snow Villiers (FF13) - MEDIGUARD STALL until Summon may well be the course of action here.
Holly Whyte vs RAGNAR BLITZ LEBRETT (XF) - Ragnar has a little bit too much damage once Hyper's in place. And we all know Holly's problems with pressure. He punches past Holly's healing a lot better than Judecca as well, which mitigates the accuracy issues to a degree.
Holly Whyte vs Sceptile (PKMN) - Holly 3HKOs Sceptile! Too bad about the insane speed split and how Sceptile can also work its way into Overgrow for a massive damage dump on her. He'll likely -need- it, but I think he can do it.
Holly Whyte vs Alice Elliot (SH1) - Alice can't really break through the healing even before you take the SP issues into account.
Holly Whyte vs Clive Winslett (WA3) - Even with Clive being -slower-, he -does- deal a lot of damage and has plenty of damage control to boot. Chipping into a powerful Gatling feels like the way to go here.
Holly Whyte vs Joachim Valentine (SH2) - Joachim doesn't have the damage for this. It's hilarious that he risks losing by running out of SP, though.
3-8. Holly swings grossly depending on your durability respect for her, since she's all about pure attrition. I'm not really sure how SnowFire scales boss HP (and I honestly see his scaling as quite generous for her specifically), but his view of her HP, which is over double mine, likely hands her a borderline Middle/Heavy nod, since that makes her healing nearly a full bar of PC HP - of course, he limits her AI to a degree, so. Given my views, though... she kinda struggles when the damage scales start climbing upwards. Additionally, the bad slugging (6HKO damage? Below average speed?) means she's more or less a Light when the healing doesn't pan out. Boss Mint, given the appropriate proportions, feels like an appropriate moniker here. Spoils low damage and limited resources, but runs into irredeemable trouble when neither of those are issues. Spiky damage can also be problematic. I at least allow her to heal at any HP range once she hits the 50% threshold once, but that limiting range can be an issue as well.
Ninja vs Palom (FF4) - Mage against Ninja. Shippujinrai x4 clocks in at 46% damage to average, which may work against FF4o Palom, but sure as heck doesn't against FF4a.
Ninja vs Jude Maverick (WA4) - Even with Ninja's speed, the defense's so bad Assault Buster's still doing a number here, and Rapid Attack is a great way to punch past Utsusemi (after all, Jude's faster than Ninja to begin with). Ninja might well be UNABLE to break through Jude's damage nulling to boot, which would just make this fight hopeless. EDIT: After Pyro's argument, I think I'm still keeping my vote here, though: it hits me that any possible Leyline hex combination in-game hands Jude a way to win through Ley Boost (having one of Wind or Earth hexes let Jude grab a decisive victory against Ninja, since he can control when to ram into Transience (do note that Ninja only even deals damage to Jude once his attack gets buffed once, Ignia Guard's property sorta means Ninja's incapable of damaging Jude before that), and only combinations where there's only one of Earth and Wind -and- Ninja starts on them lead to the initial argument. I really doubt Jude misses a 4-3 using his physical twice, though, and one RA'd Assault Buster OHKOs Ninja of the 0.67x pdur (while, even fully buffed, Ninja 6HKOs Jude, so the practical effect is likely more like a 7HKO here. Ninja needs a third counter). Of course, always tiebreaking against BD evade here - otherwise, Ninja would have this match period.
Ninja vs Judecca (WA2) - Utsusemi spam gets to shine here.
Ninja vs Billy Lee Black (XG) - Delicious Xenogears haste works out its game here. Transience counters may be annoying, but Billy has the healing and resources to make it work. Not to mention a charged Deathblow string likely one-rounds Ninja anyway.
Ninja vs Solo (DQ4) - Magic.
Ninja vs Snow Villiers (FF13) - Magic.
Ninja vs RAGNAR BLITZ LEBRETT (XF) - No magic!
Ninja vs Sceptile (PKMN) - More magic.
Ninja vs Alice Elliot (SH1) - Yet more magic.
Ninja vs Clive Winslett (WA3) - EDIT: right, alternate evade setup. Utsusemi I think I see owning Lock-On, so yeah. Sigh.
Ninja vs Joachim Valentine(SH2) - Holy crap, Joachim's magic sees use here. Welp.
3-8. This pool exploits Ninja's weaknesses quite viciously and even some of the physical fighters circumvent the evade game just fine. Utsusemi's actually more limited than I first thought, but sometimes it's just the luck of the pool.
Cordelia vs Palom (FF4) - Goes first and viciously ravages an infant.
Cordelia vs Jude Maverick (WA4) - Neither doubles, but Jude can survive three shots maximum of viable Cordelia offense (her own turn+a counter+a Javelin counter). She can't really handle a full Assault Buster String, on the other hand.
Cordelia vs Judecca (WA2) - Doubles and goes first, which does ugly things here. Judecca needs to OHKO, and he ain't pulling this off.
Cordelia vs Billy Lee Black (XG) - Doubles, goes first, one-rounding ensues. It happens.
Cordelia vs Solo (DQ4) - Solo's not 2x PC HP tanky if I recall correctly, though he's not too far from it. Cordelia mdef staves off a first turn sleep and she two-rounds while going first otherwise.
Cordelia vs Snow Villiers (FF13) - Snow can't Mediguard stall here lest he wants to explode and he loses a straight slugfest. Cordelia is frankly vicious when she doubles.
Cordelia vs RAGNAR BLITZ LEBRETT (XF) - Cordelia fails to double and has to ram into Ragnar's great evade. Losing proposition, especially when he avoids counters and can actually use Raving Rage in this fight.
Cordelia vs Sceptile (PKMN) - Hm. Cordelia has an easy 2HKO on Sceptile and she nerfs his draining to a degree with the MDef. However, Sceptile -still- 3HKOs and I see gen 3 Leaf Blade avoiding counters... and Agility should actually let him double Cordy. He also has a 3-2 on her if he goes that route, so, Agility, Cordelia turn (if she uses a Javelin for counters here, she just ends up losing anyway), Leaf Blade x4, collect victory. EDIT: hinode mentioned Leaf Blade is a contact move! In that case, better idea to Giga Drain, which still 4HKOs Cordy.
Cordelia vs Alice Elliot (SH1) - Cordelia -actually 2HKOs Alice through panties- before Gospel, and likely 3HKOs after it. Since Alice -5HKOs- Cordy, I kinda have problems seeing her actually pull this off with 13 SP to work with and the prohibitive costs on Advent: she either runs out of MP, SP or both - and I haven't even gotten to how she needs to reapply Gospel every five turns either! So it goes.
Cordelia vs Clive Winslett (WA3) - EDIT: Huh, oversold Clive's HP and undersold Cordy's damage a bit. Sure, one-rounds.
Cordelia vs Joachim Valentine (SH2) - Joachim even has a shot with the ID, but on average, Cordelia should eke this out.
8-3. The pool mooooooostly played to Cordy's strengths - against anyone clocking in at average speed or below, her offense is Heavy champ-calibur, and this roster had plenty of those. When it didn't... well.