You must be joking. How will he regenerate from a beheading? Elektra will kill and is way quicker -- and LoL, Deadpool has fighting skills "beyond Elektra's?"
How? Stick, Stone, Shaft, and Star trained Elektra. She torched Wolverine. She'll torch Lady Deathstrike. She's out of Deadpool's league in pure h2h skill. Easily one of Marvel's best earth-based h2h combatants.
Remember she walked through 8 S.H.I.E.L.D. agents? *Underwater?* And her silent scream?
Deadpool wins in durablity, but it probably wouldn't be a long drawn out fight. That's not was assassins and hitmen (my apologies, hitpeople) go for. Remember Deadpool's fight with the Cat? Shen Kuei's just a regular guy, and he took down Wade easily.
One can live without one's hand -- and how one does not see the difference between regenerating an appendage and one's HEAD is beyond me. The Hulk can't regenerate a head. Neither can Wade.
As far as hitting her, please. Wade does not have enhanced speed. Wolverine was only able to slash her thigh because she LET him. She's that quick and that good.
I think you misunderstood the hand thing, Never. He didn't regenerate a hand, his entire body grew back from a hand, because it was the largest thing left of him. Though I'm still in favor of Elektra.