For starters, I'm going to assume that Silver Samurai doesn't have his teleportation ring for this fight. Since Taskmaster's power level basically depends on what he's armed with, I'm assuming he's just armed with his standard shield, bow & arrows, and maybe a sword.
One thing you're miscalculating... (if you meant this to be a Wolverine spite thread); Team 2 is made of people who have never worked together before and would probably not get along well or preform as a functional team. Bullseye is insane, and Taskmaster probably wouldn't listen to Deathstroke's tactics. Cardiac is fairly intelligent, so he might, but Crossbones is a dumb thug.
Conversely, Wolverine and Sabretooth have worked together before, and when they do it they are nearly unstoppable. Kenuichio is hardly the badass Wolverine and Sabretooth are, but he's worked with Logan before too and he's not too proud to follow tactically sound advice. I see Team 1 choosing most of the fights here, while Team 2 attacks uncoordinated and hodge-podge.
Just for fun, let's go with the matches Beyonder set anyway.
Wolverine v. Taskmaster would indeed be a lengthy fight.
After his Weapon X upgrades, however, Sabretooth is a monster. His strength and speed are upgraded far beyond peak human levels, as is his healing factor. (He once had almost all his skin burned off and it hardly slowed him down.) Don't forget he now possesses an adamantium skeleton of his own.
Cardiac's super-strength is comparitively, fairly minor. Deathsroke's strength is peak human (only his reflexes are enhanced, due to his heightened intelligence.) Sabretooth can press upwards of 40 tons now, and in a hand-to-hand fight he'd overpower them both. Deathstroke put in an impressive showing against the Justice League in IC, but he had prep in that fight and knew his opponents extensively. Sabretooth belongs to a wholly different universe, meaning Deathstroke's going in blind.
The one thing Cardiac's got going for him are his glider and his energy staff. Sabretooth's ability to shrug off massive injury, however, means that while Cardiac is blasting him, the Canuck runs right through it and gores poor Deathstroke. (He might take some scratches from Deathstroke's swords, but it's nothing he can't ignore.) Deathstroke's healing factor isn't nearly as absurd as Sabretooth's, he'd be down and out for vital minutes after being nearly gutted.
Still, there isn't much Sabretooth can do against Cardiac. He would get brought down eventually, after enough blasts.
On the other hand, your assertion that Bullseye would kill Lady Deathstrike is absurd. Bullseye relies on the weaknesses of human anatomy to kill his targets. Deathstrike is a cyborg with no such frailties. Not only that, these days Deathstrike has a healing factor of her own. A few pins in her throat isn't going to give her the slightest pause. By contrast, one solid slash and Bullseye is down for the count. Yuriko's chances of victory in this match are assured.
As for Crossbones vs Silver Samurai... this one is really up in the air. If Silver Samurai gets within striking distance, the fight's over.... but Crossbones has a gun, and while Kenuichio's armor is tough I don't think it's bullet-proof.... still, I'm going with SS for the win, because he'll likely receive backup before Crossbones does.
Now it's Deathstrike, Silver Samurai, and Wolverine vs Taskmaster and Cardiac.
The thing about Wolverine is that here's where the sheer number of styles he's mastered comes into play. Taskmaster only needs to see a move once in order to learn it himself. As a result, Wolverine will find every maneuver he attempts thrown back in his face. He'll have to switch through fighting styles fast and improvise a lot just to keep up. Honestly, he's never displayed that kind of flexibility before, so I see him taking a LOT of punishment.
On the other hand, his strength and speed outclass Taskmaster cleanly. (Taskmaster is, afterall, just a regular guy with a good gimmick.) Not only that, Taskmaster's fake shield is useless in h2h--he can't use Captain America's shield techniques against Wolverine, because Cap's is indestructible, and Task's will crumple under an adamantium assault. The shield is only good as a ranged weapon, and Wolverine is going to be coming at Task faster than he can step back. Taskmaster will be forced into melee constantly (this also makes his Hawkeye-techs useless.)
They're both in dire straits (although anyone reading the comic would think Wolverine was on the losing end, as he'll definitely take the greater number of injuries in the melee.) Still, whatever weapons Taskmaster employs will surely break if forced to parry Wolverine's claws, and he can't keep dodging forever. I see Wolverine winning this in the long-run, because he'll keep fighting and he's at least a competent enough duelist to guard his vitals. Taskmaster won't be able to get in a defining injury that could overload Logan's healing factor, and he'll eventually wear out as the fight drags on.
Meanwhile.... Deathstrike has superhuman agility and speed to match Cardiac, but again his glider presents a problem. Deathstrike has some mad ninja leaping abilities, but she'd be hard-pressed to catch Cardiac. Plus his electric attacks might do something especially nasty to her hardware body. I see him finishing her like a Matador finishes a bull, only in this case the "Bull" is a leaping cyber-ninja and the Matador is shooting lightning out of his staff.... Kenuichio doesn't have the strength for fantastic jumps, so he's basically screwed....
Wolverine, I think, has the strength to make a leap at Cardiac (where is this fight taking place? Is there anything he can jump off of?), but it would be fairly hard for him to land a strike on Cardiac or the glider, and all too easy for Cardiac to zip back and blast at Wolverine. Wolverine is comparable to Spider Man in speed, but not quite as good. On the other hand, he could probably take at least several hits off the blasting rod. I'm going to say the final advantage under this scenario rests with Cardiac thanks to that damn glider, but you shouldn't count Wolverine out.
But like I said, if you just had them start off at separate ends of an alley 1950s Bronx-Rumble style, I don't think you'd see these kinds of matches. Deathstroke wouldn't run in at first, he'd hang back and study his opponents. Wolverine and Sabretooth would be doing the doubleteaming, not getting doubleteamed. Crossbones and Silver Samurai, as the only basically normal guys here, are pretty much screwed however it goes down anyway.
I need some evidence before I'm gonna swollow that.
