VS Crossbones, Fear Itself: The Fearless #7
It doesn't matter if you're one of Captain's greatest villains or just a random thug, bullets will never cut it against the runt. The heartless mercenary Crossbones (Brock Rumlow) took on Wolverine and the outcome left a major mess for the janitor to clean up. Crossbones is known for being a tough guy, so the villain pumps plenty of rounds into Wolverine before even recognizing that his tummy has been sliced open by Wolverine's foot-long claws. Instead of making a run for it, Crossbones arrogantly blasts a few more bullets into Logan, but Wolverine's healing factor and adamantium is too much for the thug to overcome. James slices Crossbones's gun apart and then, without any remorse for his human enemy, thrusts all six claws through the baddie's chest. Luckily for Brock, Hellstorm conveniently shows up and burns Wolverine. A small dose of magic later and Crossbones is back to full health, but the emotional scar of getting his ass handed to him by Logan has to hurt.
VS Silver Samurai, Uncanny X-Men #273
VS Omega Red, X-Men #5
There's no shame in losing to Omega Red (Arkady Rossovich). The guy's death spores can kill a person in mere moments and his carbonadium armor and coils make him an absolute pain to deal with. But Wolverine? He spits in the face of impossible odds. Despite being outclassed by Arkady, Logan makes it a fight worth remembering. The Canadian dukes it out nonstop with the Russian super soldier for nearly 18 hours before finally going down for the count. James eventually gets his revenge, though. A few years ago the runt baseball tossed the m-blade (a sword that negates healing factors) right into Omega Red's heart, allegedly killing the '90s villain.
Hulk and Wolverine have a long and blood-soaked history, but one battle stands out from the rest. Believe it or not, Wolverine actually tried to avoid this legendary battle at first. Hulk kept egging him on, and one thunderclap later, it was time for the warrior's waltz. Todd McFarlane's work makes this classic battle in the woods a gritty visual delight. Wolverine draws first blood on the grey brute and even takes him down with a horrific stab clean into Hulk's chest. But Logan's not the only one with a healing factor, and the two rush back into their dance of death. Wolverine's internal thoughts in the captions add a nice layer of depth (dealing with man vs. beast; the pain in his body and all that jazz) to this must read Hulk vs Wolverine battle.
VS Sabretooth, Uncanny X-Men #213
If I could only read one Sabretooth (Victor Creed) and Wolverine fight, this brutal mesh of claws and stabs at the X-Mansion would be my pick. Victor humiliates Rogue and Psylocke before making his way to the main event: Wolverine. What happens next is one of the most epic stalemates in comic history. The two go blow for blow as they duke it out across the rooftops, plummet into the pool, and continue their absurdly violent bout towards the edge of a cliff. Both bruised and bloodied, Sabretooth tries to escape the X-Men by diving off of the ledge, but Wolverine quickly follows and grapples him before the two crash into the waves below. In true villain fashion, Sabretooth manages to escape.
VS Deadpool, Cable & Deadpool #44
The merc with a mouth has a handful of solid encounters with Logan, but their swords vs. claws round at a HYDRA base is my pick. This 3 page fight is fairly short, but it's so very sweet. It gives both characters proper credit as they display just how skilled they are with their respective weapons, but ultimately, those two blades can't compete with Wolverine's six adamantium claws and the pointy things end up pinning Wade to a wall. The comedic banter from a Fabian Nicieza written Deadpool (Wade Wilson) is always a joy, too. Oh, and then there's Bob, Agent of HYDRA and Weasel in the issue.
VS Captain America, Wolverine: Origins #4
Seeing the American super-soldier and Weapon X project duke it out is a fanboy overload for many. Despite their popularity, these two fan favorites have only had a handful of fairly short fights, but their battle in Daniel Way's comic overshadows the other fights these two have had. Lasting multiple pages, the two A-listers inflict seriously damaging injuries on each other and Cap even slashes Wolverine across the chest with the m-blade. A legless Nuke (courtesy of Wolverine's claws) and the X-Men eventually interfere, but this melee is terrific.
VS Spider-Man, Spider-Man versus Wolverine #1
The wall crawler is faster and stronger than Wolverine, but that didn't matter very much in this comic. Wolverine's confidence and flurry of claws made Spider-Man question his own abilities and even his own speed. However, the reason this throw down happens is the true gem of the comic. Wolverine is going to kill Charlie, a woman he cares deeply for. She's on the run from just about every government on Earth, and Logan was going to give her a painless end instead of torture from the KGB. But Spider-Man and his heart of gold step in and stops Wolverine before he can end Charlie's suffering. Spider-Man bashes Wolverine's face over and over against a tombstone, but he says the only thing the brutal strikes did was make Logan smile. They end in a draw, with Spider-Man's hands gripped around Logan's throat, ready to snap his neck, and Wolverine's fist under Spidey's chin, prepared to pop his claws. A helicopter shines a light on them, and in the confusion of the chaos, Spider-Man throws a blind strike when he thinks Wolverine is behind him and ready for more. Yet it wasn't Wolverine standing behind him; it was Charlie. Spider-Man ends up killing the very woman he just fought to save. Ouch.
VS Sabretooth, Wolverine #301
It looks like Sabretooth has returned from the dead just so he can get his ass kicked all over again... and I must say this is a jaw-droppingly good ass kicking. Seriously, it doesn't get much better than this. I'll let the page speak for itself. Stare at that image and enjoy just how awesome this victory truly is.