Oh man, this is such a good match. I love it.
Round 1 is really tricky. I want to say Harry takes the majority, but it really depends on how things play out. A good writer could easily make either outcome believable. I feel like Taylor is able to find Dresden first. Harry would really need something of Taylor's before he can do a tracking spell, so I want to give Taylor the initiative here. (Although if Harry can pass into the Nevernever to get around New York, Taylor's won't be able to track him easily at all. It could really go either way.)
Anyways, if Taylor gets the first move, she'll probably sneak some of her more dangerous bugs onto Harry and try to stop the fight before it even starts. She's pretty much always bloodlusted, so this wouldn't really be out of character for her. However, if Harry knows the basics of her power, he could probably set up a shield or a ward to keep bugs off of him.
If they see each other, then things really start to get interesting. Harry can hold of a swarm pretty much indefinitely between his shields and his field of cold. On top of that, he has no shortage of big fiery AOE attacks. He's going to rip through Taylor's swarms like nobodies business. In a direct confrontation, Harry wins, hands down, barring some serious prep shit from Taylor. Even then, I don't see Taylor taking Harry down. He's too savvy and Taylor has no allies.
What's more, I don't think Taylor can even retreat once Harry sees her. While they're both good runners, Harry is fairly superhuman thanks to the winter mantle, and he's a PARKOUR expert. On top of that, hunting and chasing prey is pretty much the Winter Mantle's schtick. Taylor isn't getting away.
Now, here's what makes this round interesting. Harry has a noble streak a mile long. He's not going to go hardcore on Taylor if he recognizes her as a teenaged girl. No way no how. That's just the sort of advantage Taylor would push. She'd pull something dirty, and surrender to Harry or something, and then bash him on the head when he looked away. So, she could win some of the time pushing that advantage. Not a majority of the time, I think. There still a massive physical disadvantage, and if Taylor knows this much about Harry, then Harry probably knows a decent amount about Taylor. He's not going to let his guard down too much.
However! If Taylor doesn't know about that little facet of Harry, then it doesn't matter. She's a scary motherfucker in costume. She doesn't look like a person, she looks like a demon insect, in the middle of a swarm of bugs. Hell, it's been explicitly stated she wouldn't look out of place with the Slaughterhouse 9, a group of superpowered serial killers. If she goes into battle like she normally does, there's no way Harry is going to think "Oh, that's just a kid, I should be nice." and he swats her down.
So, depending on how much they know about the other, round one is really interesting. If they don't know much about each other, then Taylor can sneak enough bugs on Harry before fighting that he goes down with no conflict. If Harry knows the basics of her power, I think he can force it into a direct confrontation, which he wins, 9/10. He's pretty much a hard counter to Taylor in a direct fight. However, if Taylor knows quite a bit about Harry, she can change her strategy and play on Harry's chivalry. Harry's instincts are still good, so I still think he takes the majority, 7/10. (He's still the fucking Winter Knight, and if Taylor knows that much about Harry, Harry probably knows enough about Taylor to keep his guard up, so there's still a lot of luck involved in taking Harry down.)
Round 2 Harry stomps this one very very hard. Taylor's only hope is taking Harry out before the fight starts, and that's only going to happen if Harry doesn't know she uses bugs. If Harry doesn't know she uses bugs, then Taylor wins 6/10. (Harry's still good at finding people, and Taylor has to be somewhat nearby to use her bugs.)
If Harry knows to be on guard for bugs, then he takes it 9/10 or 10/10.
Round 3 The biggest change is that Taylor might be able to lure Harry into a trap or she might be able to escape a direct confrontation. If Taylor gets her non-superpowered allies, she probably takes the majority 7/10. With all her allies, 9/10 or 10/10 in her favor. If Taylor gets no allies, Dresden still probably takes 6/10. He's very savvy, more versatile, more experienced, and he hard counters Taylor. While Taylor is devious enough to play her homefield advantage to great use, but I don't think she takes the majority without more help.
Round 4 This doesn't actually turn this into too much of a stomp. If Harry doesn't get allies, then it's basically the same as New York, with Harry getting an autowin by making it to Demonreach. He rushes to Demonreach, and wins 99/100. (9/10 he makes it to Demonreach before even fighting Taylor, and the 1/10 times he does meet up with Taylor, he takes those 9/10 times.)
If Harry does get allies, then it changes things. If Taylor knows enough about Harry, then she probably just takes Murphy or someone hostage, and Harry surrenders outright. Taylor takes that round 5/10.
If Taylor doesn't know enough to take someone hostage, then Dresden roflstomps 10/10.
Bonus Round depends on the context of the fight. If it's something very important, Harry's noble enough to die before he gives up. I don't think Taylor goes quite that long. If it's just a fight, then it's probably a tie.