The Gauntlet of Wade Wilson
Yes, yes, many in the middle are debatable as far as order(I tried to arrange this in the order I thought was appropriate; you want to ***** about it? Do it elsewhere, 😛. ) goes - if it is bothering anyone, just list how many wins you think each gauntlet opponent or deadpool would win out of ten, and we won't have to worry about the order.
Deadpool gets his standard arsenal - swords, guns o plenty, grenades, and etc.
Not that he particularly needs long to rest, but he is fully healed before each battle, and his supply of ammo/grenades is restocked.
Each of his opponents is carrying whatever they would on any normal occasion.
1. Kingpin
2. Bane
3. Punisher
4. Nightwing
5. Lady Shiva
6. Elektra
7. Batman
8. Daredevil
9. Deathstroke
10. Cable (No Telepathy or telekinesis)
11. Black Panther
12. Iron Fist
13. Mr. X
14. Taskmaster
15. Captain America
16. Wolverine
17. Agent Zero
18. Spider-man
19. Venom