Ok. This actually seemed pretty interesting.
First. Equalize speed
I went around to other threads to get a good vibe on what he does. Mostly to see if he opens with time stop, which it shows he doesn't always do so. Mostly do to his arrogance.
Dios biggest issue he is gonna have is a Boo comes on and he is screwed. He has no fear hacks resistance. Let's go over a few openers for naughty
If he opens with Boo, Dio runs away. Plain and simple. Naughty May shoot him in the back while he yeets himself away. Or he may not care. Either way. A win
If he opens with range. Lightning is also a pretty bad thing for Dio. As since it doesn't come from naughty himself, it comes from above, which Dio wouldn't expect that. And his overconfidence and arrogance can likely add onto that. If (and this an If), the Golden Oozy hits Dio, Goodnight Dio. Naughty is physically superior, and his own gun can tear himself apart. If it touches Dio even once, it's gonna put him down. However, tagging him directly is gonna be pretty hard due to his stand. Assuming his gun couldn't hurt Dios stand, Naughty would definitely know something's up. When it doesn't work, there's no reason Naughty would continue with that tactic. This would leave him to either zoom to get out of his line of site and take a stealth and trap like approach, and or Boo him away. Likely the latter since he is such a fear hack like person
If naughty decided to be stealthy, if he does get out of dios site. It's over from there. Naughtys stealth lets him GG, with a trap that can kill people superior to his level, or sneak attacks him with whatever he wants. And no way he losss track of where Dio is. His Senses and powers say no to that. But Dio finding naughty will be difficult
Dios time stop is a good power, and can certainly get him wins. But I'm betting on it less than Naughty is to resorting to fear tactics first. Naughty is direct, he doesn't screw with people. When he does for the kill. He is quick about it. Dio is arrogant and Over confident. This definitely leads him not to open with it as many times as he could, and leaves him far more open for naughty to end. Naughty simply resorts to his instant win faster, isn't arrogant or overconfident, and is much smarter. His skills are immense. He can fight with robots designed to kill him by a person so smart, they built a machine that can cross dimensional planes of existence. And he beat multiple of his robots to death, with a stick. And if naughty at any point ends up in front or close to Dio. He taps him and then Dio faces the same fate Jotaro faced against kenshiro. PP turns him to dust. And Naughty has one potential way to lol no his stand if the stand qualifies as a spirit. Which the Carmichael knife controls him. Or can remove him. (But not sure on that one)
But before I leave my vote. Let's take a look at Dios case when he does stop time pre to naughty doing something to stop it. This doesn't exactly promise a win. Naughty is physically superior to Dio, and Dio is at his furthest at the time. With only 5 seconds, he isn't gonna likely do the damage needed to end Naughty. The hacks he does have that could win like mind hacks aren't in character. So he wouldn't have to immediately just start laying ham on naughty the moment those 5 seconds are going. And his attitude just doesn't lead him to do that.
So going Naughty. Skills, Versatility and more options to win, Haxs, harder to predict, quicker to use his if not open with his best win conditions, Far less arrogant and over confident, intelligence, stealth, potential way to deal with his stand, More in character win options, and physicality
