I still believe they could surprise him Wolverine is an experienced hunter he imo could sneak attack Superman. Also they both they prep time to kill Superman. Deadpool cuts his lower body off calls for help putting the sword beside him and when Superman comes in from Wade's screams he gets close to Deadpool to get him to the hospital and gets a blade in the cranium.
I think Deadpool has the edge because of his 4th Wall awareness/slap-stickery which would likely allow him to know about Superman's weaknesses and procure some kryptonite. He'd likely ingest the kryptonite, try to sneak up on Superman, fail miserably, and while Superman is being dismissive of Deadpool's inept attempts and annoying antics Kal's getting weaker from being in proximity to Deadpool and Wade eventually lands a blow.
But before he can land a killing stroke Bruce and Diana show up and Deadpool gets lasso'd and punted to Brazil.
Yall would make horrible assassins. Clark Kent can be distracted. Either using his job, innocent people, are those he cares about. He doesent run around supersniffing everybody and I doubt that if he smells unknown metal hes just gonna go on the attack. He doesent run around the streets of Metropolis at ftl, sniffing and x-raying peoples crotches. Hes not Krypto.
In a fight, obviously they have no chance. But thats not what the op is asking, can they sneak up on him with a one shot kill weapon. There is different ways to sneak, you dont have to low crawl through the shadows to sneak up on someone. They have 3 weeks to prepare. Im pretty sure that two of Marvels top killers can come up with a better idea than walking down the street swingin a sword at people.
Not a chance for either of them. Your 'upgrades' are like pitting 2 toddlers against an Olympic gold medal heavyweight boxer, then saying that they will make a fight of it if you feed them both a couple of protein shakes and kit them out with some giant comedy boxing gloves.
'20 ton strength boost' and 'cuts-anything sword' are ridiculous when up against Superman, even in some of his weakest incarnations.