9. Getting Crushed By A Steamroller
Wolverine and the Punisher have worked together on numerous occasions, especially in the late nineties and early 2000s.
Although the two are an effective team, they often come into conflict. Frank Castle often clashes with other heroes, like Spider-Man and Daredevil, but when he clashes with the Canucklehead, Frank uses more brutal methods because he knows the X-Man can handle it.
During Garth Ennis' initial run on Punisher, the two characters cross paths, both thinking the other is responsible for a series of Mob murders. It's not long before the Punisher gets tired of Logan's antics and decides to park a steamroller on his head. The steamroller alone would be bad enough if Frank hadn't already used a shotgun to blast off his face, and also a machine gun on his nether regions.
Though this encounter with the Punisher might not have caused the most long-lasting of injuries, it never the less will be a sore spot for Logan. It's hard to forgive a guy that crushed you with a steamroller.