Holly (The Wizard of Oz: Beyond the Yellow Brick Road) vs Tir McDohl (Suikoden Series) - Good news for Tir: he can probably tank two Magic Charged Fireballs. Bad news: he's slower and he doesn't have much recourse against Dream Land. He can't live through a full sleep string and she's landing it in three attemps on average -if- you see his mdef affecting her Sleep odds. Otherwise, it's even easier. If you see her living through two Judgments (I don't), this isn't even a question.
Mikhail Ausbach von Loanne (Romancing SaGa 3) vs Kyra Tierney (Phantasy Star IV: End of the Millenium) - Hoooooooooooooooly crap, what a stallfest. This involves factors like ROMANCING SAGA 3 STATUSBLOCKING OPTIONS, PHANTASY STAR 4 SLEEP, STAT DEBUFFING TO VIABILIZE INSTANT DEATH ODDS (since, at base, Kyra reduces Mikhail's match-winning status odds to 0 but they rise once he manages to debuff her speed - which doesn't go through the same stat check process as his status) and possibly even LIFE CANE'S INFINITE HEALING. Dear god, CK.
EDIT: OKAY, let's begin. There's a storebought helm that lowers Mikhail's defenses slightly and grants him sleep immunity (THIS IS IMPORTANT, since PS4 sleep -matters- in long stalling matches). This lowers his speed by 2, so now he's below average speed and Kyra's above. HOWEVER, she's going to run out of offense long before killing a sleep-immune Mikhail (Illusion Sun, Power Heal and the odd Revival Light casting if she gets ahead on damage early all mean she can't purely out-attrition him by force) if she goes for two shields, so she -needs- a weapon... which gets her 2HKOed by Final Letter. So, she also needs to open with Warla. And gives Mikh a turn to open with Illusion Sun. Losing the mdef from a Psy Shield, she also now becomes effectively vulnerable to Midas Hand (since Midas Hands was initially something like 4% accuracy going by PS4's subtraction system). The match just suddenly became a lot shorter. Buuuuuuuut she's still faster than Mikh, and now by an appreciable margin. This could go on for weeks. I'll get back to you on this.
(And no, Escape Out isn't a factor. Too much of Kyra's offense is MT.)
EDIT 2: Man, good thing Kyra also has Telele, otherwise SCREWDRIVER's female weakness-hitting would become relevant due to being ITD and I'd have to calc its damage. Granted, I may have to do that anyway now.
EDIT 3: MIKHAIL HAS PARALYSIS RIGHT. Holy shiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiit, nevermind. I'm pretty sure this tilts the match in his favor, since he can mostly paralysis-lock once he lands it once (he should take something like three attempts to do so, and he gets a lot of time to apply it). Granted, Kyra recovering on an occasional double would be an additional annoyance, but Mikhail's winning this through status, not outresourcing. He's just happy his status options are so staggeringly cheap and the fact he runs off two distinct resource pools. I'm slightly weirded out by Mikhail's duelling complexity now.
Malak Galthana (Laggy Fantasy Tactics) vs Dragonite (Pokémon) - Exploding Frog.
Madchen (Dragon Quest V: Hand of the Heavenly Bride) vs Nina (Breath of Fire II) - Jiggle physics.
Cistina Phoraena (Tactics Ogre: Let Us Cling Together) vs Ashton Anchors (Star Ocean: The Second Story) - Cistina's pdur is kinda nuts and Healing Infusion kinda drives the physical tanking further home. Ashton even has good enough damage for this to not be very sad, but it's an uphill battle still.
Cai (Brigandine) vs Anna (Fire Emblem: Awakening) - Cai effectively 4HKOs (after factoring in evasion) and loses the initiative tiebreak. Anna 5HKOs to me (GE for me, so Cai doesn't resist Thunder), Cai's mdur is effectively average... but he has healing, and 2HKOs at base even with his cheap damage (Exa-blast is just cost-inefficient here). Yeah, think he can pull this through. Anna doesn't want to brave melee counters either, since her damage with physicals is -even worse-.
Tin Man (The Wizard of Oz: Beyond the Yellow Brick Road) vs Pikachu (Pokémon) - I think Tin Man OHKOs even if he misses one hit from Battle Wind due to Double Team. Yeah no.
Baybull (Super Robot Taisen J) vs Pierre (Chrono Cross) - sure evade
Sunset (Live a Live) vs Kain Highwind (Final Fantasy IV) - Sunset just plain outslugs because Kain's damage is just that awful (as in I think he -3HKOs- with Jump. Seriously). Jump means just unloading his charged damage, which risks OHKOing him flat.
