The first meeting between Wolverine and Deadpool ended with a decisive loss for Logan - but only because Deadpool cheated in the worst possible way. Wade Wilson and Wolverine both have two of the most powerful healing factors fo all mutantkind; they allow each man to survive a hail of gunfire, sword strikes, and even blows from far larger foes. There was no chance the first meeting between the two wouldn't end in a fight - but the result was quite controversial for Wolverine fans.
While Wolverine was already an established character in the 90s with a solid backstory, personality and a solid grasp on exactly how his powers worked, but Deadpool was quite new. Debuting in 1991 in The New Mutants series, Wade Wilson was a neophyte newcomer to superheroics, and lacked much of the morality he has today. This is most like the reason why Deadpool spontaneously attacked Wolverine when they first met - and why Deadpool had to resort to cheating in order to claim victory.
Released in 1994 just three years after Deadpool's creation and debut in The New Mutants series via creator Rob Liefeld, Wolverine #88 involves Deadpool as a guest star, albeit a guest star who takes center stage. Deadpool is on the hunt for Kane, who is currently dating his ex-girlfriend Vanessa (then known better as Copycat). Wolverine and Deadpool slice each other with their claws and katanas, respectively - but Wolverine's healing factor isn't working as quickly or reliably as it usually does. Deadpool stabs Wolverine in both lungs and retreats, leaving Logan lying on the ground.
Deadpool Had To Cheat To Beat Wolverine
Deadpool is a master assassin (at least in this time), but Wolverine has fought hundreds of foes, and is far older than Deadpool could ever suspect. 2001's Origin, the story of Wolverine, would eventually reveal he was born in 1835, making him over 160 years old at the time of this story. With over a century of experience fighting foes far stronger than Deadpool, the Merc with a Mouth had no choice: he had to cheat and exploit Logan's then-waning healing factor in order to even stand a chance.
The end of the story would eventually see Wolverine save Vanessa from Deadpool's wrath by taking the sword thrust meant for her. Deadpool escapes this awkward situation, but Wolverine is stuck with the pain, both physical and emotional. Deadpool and Wolverine are fierce combatants who can heal from nearly any attack, but only one of them had the experience to fight the other - and the other was dishonorable enough to cheat.