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A pretty heavily-discussed vs. topic elsewhere, considering it was one of the first suggestions when I google searched Kiryu's name.

Both are pretty much top-dogs in their crime-ridden cities (Kiryu's only real equal thus far appearing to be Taiga Saejima) and both are shown to be both brutally pragmatic in their styles in addition to their formal training.

Two scenarios:

First fight is a straight up hand-to-hand in a fighting ring with no other parts of the environment to use as weapons

Second fight takes place on a city street with whatever environmental advantages it can offer them both.

And some vids of them in action:

Kiryu (as of Yakuza 5)
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Wei Shen
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Barring the flashier nature of Yakuza's combat, I'd still give the edge to Kiryu. By how much, I'm still thinking about, but I say his advantage comes down to his clearly larger and stronger build, being barely if at all less agile, and having arguably more experience and resilience (he fought two tigers with a relatively fresh wound).

Wei Shen's definitely more brutal and lethal when it comes to using the environment (Kiryu rarely if ever kills his opponents ouright), but I think the question is if he's even strong enough to really maintain that kinda control on Kiryu like he can against the mooks who are usually much closer in size to Wei Shen himself than Kiryu. I think I'd also give Wei Shen an edge in terms of firearms skill, since, aside from that one car shoot-out section in Yakuza 1, Kiryu's most excessive use of firearms was in the non-canon Dead Souls.

Can't comment on the fight itself, since for all I know, Kiryu's probably skirting around low meta, unlike Wei's who is a street level human (bullet-time mechanics and jumping from car to car aside).

However, I'd say Wei Shen is more resilient. He had been tortured, stabbed, and was bleeding when he stomped through most of Big Smile Lee's henchmen.

Kiryu, almost routinely, tends to go through simliarly large gauntlets-arguably larger-and once or twice has done so with, again relatively fresh wounds. He was enduring stab wounds all throughout his raid on a deathtrap-infested Osaka castle before fighting the two aforementioned Tigers, and in Yakuza 5's supposed final boss (if I can find the video and you don't mind semi-spoilers), he has a wound that clearly re-opens partway through the fight, all while fighting a guy who, for all intents and purposes, would probably break Big Smile over his knee.

((then there's Saejima, who took out a bear three times his size in the middle of a blizzard)).

I haven't played the Yakuza series, so quite literally all I have to go on are the videos and info you posted. srug

You'll have to forgive me for saying Wei Shen was more resilient because all I knew was that Kiryu had taken on two tigers while wounded.

How bad are the wounds he gets?

The worst (or at least most at once) I remember him getting was probably within flashbacks actually, most of which from Yakuza 1. He was also tortured in said flashback and I'd say the worst for wear he's eer come to was at the end of Yakuza 3 against a guy who, though relatively close to Kiryu in size, was able to earlier floor a much larger character, who was able to rip out what seemed like giant stone decorations from a wall to try and beat Kiryu with in an earlier boss fight. I'll try to find the videos and see if Sleeping Dogs had anything similar.