He can't cut her to ribbons faster than she can react, his speed advantage is nowhere near that high, he only has a + on her in Agility and he's never used Dromeus to speed blitz a servant before so clearly it isn't unreactable, and you are totally ignoring Achilles's personality.

When he fought in Apocrypha there were times where he stopped to snark because he's confident in Andreias Amarantos, and with her Divinity being at a level best stated at "basically not there" he's gonna be confident that she can't do anything, and then she can use either instant win, which she only held off from in FSN because she either had 0 energy because she'd been cursed to have to deal with Shinji, was fighting people Sakura seriously didn't want to harm and knew Sakura would HATE her if she actually killed, or fighting someone who could resist both Cybele and Breaker Gorgon.

She's bad aginst Cu because Cu is a monster slayer and she's a monster, Achilles is a human killer.

Okay now this is something I can agree on more, I forgot that Cu was a monster slayer because it's hardly ever brough up, and I was thinking Achilles could speed blitz considering the fight with Atalanta alter were he charged right at her and ran her through. Admilty yes I did forget that this man is confident in his Andreias, so yeah now there is a more believable chance that she can get him espicly if he doesn't realize in time. I would honestly say it's 50/50 between the two of them, because lets face it this is bascialy only a fight between Medusa and Achilles as both would wipe out Iskandar and his army and Astolfo, well he's Astolfo. he's got some impressive feats but he is not winning against Achilles or Medusa.

Astolfo has a lot of useful tricks, but he's not great in a straight up fight 1v1 against an actual 1v1 expert.

Iskander would 100% fall for Cybele, and his army wouldn't be too dangerous for her seeing as she could just use Belerophon or literally just use her speed to avoid them until she can kill Iskander and make the Reality Marble drop. DO I even need to point out that Ionioi Hetairoi is, let's be real, useless against Achilles even if he didn't have his Chariot he could use to just run them over.

Atalanta was midair so she couldn't use her speed, was completely insane, and he still took hits doing that.

Yeah Ionioi Hetairoi is good for overwelming someone with numbers if they can't handle it or against another group, but Againts some like Achilles it's just a warm up for him, none of them can harm him, he's faster than all of them, fought in the trojion war and is the second strongest hero in Greece being only second to Heracles, But yeah Achilles and Medusa would absoluty slaughter Iskandar, his army and Astolfo. Thank you for clarfiyfing, I knew was insane at the time and that he took hits, but I honeslty though she was on like a piece of rubble or something.

Achilles being cocky about Andreias Amarantos isn't generally a flaw, he can't be harmed by a vast majority of Servants, and even if he does get hit and injured he isn't less able to heal it and as long as it doesn't hit his heel he still has his protection.

Atalanta was in freefall when he ran her down, but given the whole scene she may very well have knocked herself off the top of the pillar she was on from the recoil of firing her bow, or the explosions of her arrows when Achilles threw Diatrekhōn Astēr Lonkhē at them knocked her off, but she was freefalling.

You probably forgot Cu was a Monster Slayer because he's also a human slayer. He's an everything slayer. If he sees it he will absolutely try to kill it, and generally he's got good odds.

Yeah so it comes down, is Achilles going to realize in time that he can't toy around with Medusa, or his cockyness about Andreias Amarantos going to get him turned to stone.

If he realizes who she is and what she's going for he's got a good chance, but since she can probably get like, 5% damage through Andreias, he'd likely stop to talk.

The way I see it playing out is she hits him while he's, I dunno, bullying Astolfo, it does little more than fuck all, he, let's say kicks her away, follows after her to talk because wow she's sure legally got some divinity, she drops Breaker Gorgon while she's recovering because she now knows she can't win this in a normal fight, and then all she has to do is look up at him, and if he doesn't immediately realize she's Medusa, which I don't think he would since he likely would expect a monster, not a beautiful woman, he doesn't look away, close his eyes, or otherwise avoid seeing Cybele, that's it.

I could see that playing out espicly when you consider that one of this man's likes is "Pretty girl's smile" and he can't use his spear's effect against women or people weaker than him, honestly another way this could go is Achilles bullying Astolfo as he sees some of the army have been turned to stone as he pieces together who Medusa is and then figures out what he has to do.

The way I see it playing out is that Achilles went after Iskander first. He gets dropped in a field or arena or wherever the fight take place and sees his opponents: a tall very attractive lady (avoid hurting), Astolfo: who even if he can figure out is male he's probably gonna think isn't a good fight, and a towering warrior with a massive grin on his face who's clearly raring to go. So it opens Iskander vs Achilles, and maybe Medusa vs Astolfo, or maybe Astolfo gets distrcted by the cool fight and Medusa decides to bide her time because she isn't an honorable hero.

Achilles and Iskander have fun, but Iskander has no chance, and so at the end Achilles sees either just Medusa who killed Astolfo by non-Cybele means (while they 100% work, she doesn't need them to kill Astolfo, where they are her only real wincon vs Achilles.) or Astolfo now wanting a fight and the pretty lady clearly having gotten into cover, and well, either scenario I said above or while he's hesitating to attack pretty lady she stabs him and it advances as the bullying Astolfo scenario after Medusa hits Achilles.

Honestly both are highly probabale as we know Achilles doesn't like to fight women, unless he has to like with Atalanta in Apocrphya.