Punisher and Wolverine are both known for a few things, ruthless, crazed fighters, mentally disturbed, and neither of them really play well with others. It only follows that they’ve met up before, and they didn’t like each other, at all.
Punisher #16-17 released by Marvel Knights in 2002.
During this story arch a bunch of mobsters are going missing, or all that’s being found of them is their severed legs. The Punisher is not only looking for the killer but the mobsters and naturally he thinks that since mobsters are getting hacked to pieces Wolverine is a suspect. Unfortunately for both of them Castle is wrong, they were both just pursuing a lead into a mine/construction area.
At this point they’ve both gotten on each other’s nerves and Frank knows full well that he can’t kill Wolverine, but instead tries to slow him down. Castle’s first attempt is by no means subtle, each uses a shotgun to blow Wolverine’s face clean off his adamantium skull.
When that doesn’t slow Logan down, at all, he confronts Frank. The two brief exchange words when Castle catches Logan off guard and shoots him directly in the groin, destroying Wolverine’s testicles leaving him writhing on the ground. No man can stand up to a testicular onslaught like that, regardless of a healing factor or not.
But not only does Wolverine keep going, Punisher doesn’t get anymore subtle, he goes all out and gets himself a steamroller. While Wolverine is getting himself together, while threatening Frank non-stop, Punisher slowly pins him under the giant steamroller. Crushing him and holding him in place, but not killing him, just keeping Wolverine out of Punisher’s business for a while.
Frank goes on his merry way to hunt down and save, then subsequently kill, a bunch of mobsters while Wolverine’s muffled screams of pain and pure anger are coming out form under an enormous steamroller.