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Run away Slendy has Perception Manipulation and Pain Manipulation, so that should help.
Cuphead, being the stubborn child he is, will try to fight even when in immense pain, as shown in his fight against Shovel Knight. If Cuphead's vision is blurred, he has Homing Attack via Chaser.
 
As the #1 Slenderman enthusiest (totally don't @ me on that). Slenderman takes this.

Teleportation has yet to be brought up, but its really damn good here. Keeping Cuphead close to him for strikes before eventually killing him. The starting distance being five meters also means that Cuphead's vision will likely be blurred as soon as the fight starts, as it's a passive thing and not something Slenderman has to actively... activate.

Slenderman's teleportation also makes him fully capable of dodging all of Cuphead's projectiles outside of the homing ones. But outside of that Cuphead has no reliable options, in melee range, which I'd consider five meters to be a roughly even ground between melee and ranged distances. Cuphead has no options whatsoever.

Slenderman essentially just has to teleport up to Cuphead and impale him with a tendril to win, enough said.
 
Teleportation has yet to be brought up, but its really damn good here. Keeping Cuphead close to him for strikes before eventually killing him. The starting distance being five meters also means that Cuphead's vision will likely be blurred as soon as the fight starts, as it's a passive thing and not something Slenderman has to actively... activate.

Slenderman's teleportation also makes him fully capable of dodging all of Cuphead's projectiles outside of the homing ones. But outside of that Cuphead has no reliable options, in melee range, which I'd consider five meters to be a roughly even ground between melee and ranged distances. Cuphead has no options whatsoever.
As I've previously said, Cuphead would probably use Chaser as soon as his vision blurs. If Slenderman gets up close, Cuphead will use point-blank Charge shots as seen in his fight against Shovel Knight.
Slenderman essentially just has to teleport up to Cuphead and impale him with a tendril to win, enough said.
Cuphead will use Smoke Bomb to dodge close-ranged attacks, as seen in his fight against the robots and against Shovel Knight.
 
As I've previously said, Cuphead would probably use Chaser as soon as his vision blurs. If Slenderman gets up close, Cuphead will use point-blank Charge shots as seen in his fight against Shovel Knight.
For the former, given how you've previously described Cuphead as a "stubborn child", I really can't see him having this kind of strategic idea to automatically swap weapons, from what I know he'd most likely just continue to shoot with his normal projectiles. Which once again Slenderman can easily teleport away from.

For the latter, Slenderman does have access to multiple tendrils at once, so he can easily catch Cuphead offguard with multiple at once. And this still doesn't stop him from using his pain manipulation, which given it's description, it, while a bit vague, can mean a ton to Slenderman's victory. Possibly incapacitating Cuphead so he can't move.

This is all without mentioning that he has no real way to bypass Slenderman's regeneration outside of Charge Shots, which can maybe blow Slenderman up. But once again, I only see Cuphead starting with the Peashooter, which won't do him any good before he just gets stabbed multiple times with Slenderman's tendrils
 
This is all without mentioning that he has no real way to bypass Slenderman's regeneration outside of Charge Shots, which can maybe blow Slenderman up. But once again, I only see Cuphead starting with the Peashooter, which won't do him any good before he just gets stabbed multiple times with Slenderman's tendrils
As shown in the first 5 minutes of Indie Cross, Cuphead opens with a Charge shot. Cuphead also likes to use Smoke Bomb to get the jump on his enemies. Though Slenderman's other stuff makes this seem kind of stompish.
 
Even if he were to get the jump on Slenderman, which isn't really possible since both are. kinda aware of each other? this isn't a case where he can just oneshot Slenderman and be done with it. Within the first hit he does after getting the potentail jump. Slenderman will likely just, turn to where he was hit and be able to kill Cuphead then and there
 
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