During Marvel's first Civil War event, Deadpool hilariously tried to play a dumb trick on Daredevil, believing that he almost got the drop on the Man Without Fear. However, it turned out that Wade Wilson wasn't even close, and he only served to make a fool of himself (his usual default). Still, Deadpool's attempt wasn't any less hilarious, providing a super unique showdown between the two heroes who couldn't be any more different in the Marvel Universe.
During the first Civil War, Wade Wilson elected to operate as a bounty hunter for the government, helping to bring in any unregistered and powered individuals. However, many of the first heroes he went after had already been registered, resulting in some very humorous and awkward encounters. Eventually, Deadpool was able to determine the location of Daredevil, seen in the Civil War tie-in issue Cable & Deadpool #30 from writer Fabian Nicieza and artist Staz Johnson, and it's here where Wade Wilson's trick didn't go exactly as planned.
In the issue, Deadpool tracks Daredevil down to a warehouse once he's sure that the Man Without Fear hasn't registered with the government. While Daredevil did get the first hit with a surprise attack with one of his billy clubs, Deadpool ends up sticking him with a device o his back he refers to as an "interspatial distorter," which he claims is capable of "phasing his brain temporarily to Dimension X". However, Daredevil instantly determines the truth behind Wade Wilson's pretty dumb (yet hilarious) trick:
While Deadpool seems to take some pride in thinking that he pulled a fast one on Marvel's resident blind superhero even for a brief moment, the best part of his dumb prank is that this particular Daredevil isn't Matt Murdock. Danny Rand's Iron Fist was filling in as the Devil of Hell's Kitchen during this time, meaning that he could clearly see what Wade was up to from the start, adding a hilarious dynamic that Deadpool doesn't figure out until he's already surrounded by Captain America and more heroes from the anti-registration movement.
In any case, Deadpool's attempt to prank Daredevil failed spectacularly and hilariously. Despite the fact that he thought he almost got him, he never even stood a chance against this alternate Man Without Fear. Regardless, seeing Wade Wilson taking on any version of Daredevil is pretty entertaining, and it's certainly one of the funniest showdowns that occurred during the tense battles the first Marvel Civil War featured as it progressed. However, seeing as how Deadpool's trick was essentially wasted on Danny Rand, one has to wonder if he'll ever try his iPod gag again with the real Daredevil at some point down the line. It would certainly be a funny callback.