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Since Slappy has too much has, I was thinking of having his brother fight Chucky instead.

Mr. Wood vs Chucky

I know Mr. Wood scales to better physical feats, but Chucky has the experience advantage as well as his Voodoo magic and body control. This will probably be a battle of strength versus skill. Battle is in an abandoned house. Both fighters start unarmed, but the kitchen is full of knives if they can get there.
 
Honestly, I fail to see how this isn't a stomp. Experience (Said experience coming from him murdering non-supernatural humans, with the occasional possessed doll with non-combat applicable powers) can only get you so far when your opponent is hundreds of times stronger than you, so much so that they could reduce you to mush in a singular attack (said opponent is not afraid to take lives, as he was so much of a bastard that he threatened to kill someone's pet dog, and would have done it if he wasn't interrupted). The only useful advantage Chucky has here is reaction speed, but he can't dodge Mr. Wood forever, given Mr. Wood is an organless being that would never tire. So eventually, he would get sloppy and that would be game over.

Not even Chucky's magic would be useful here. All of them require drawn out rituals that can be easily interrupted, and if he wanted to possess Mr. Wood (which wouldn't be possible since in the show it is established that when it comes to dolls, he can only possess Good Guy dolls, but lets ignore that for a bit) he would need to first incapacitate him somehow to do it.
 
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The OP didn't clarify which tier Mr. Wood would be at in this battle.

For 9-B, his Joule value is 4.088 Megajoules (To clarify, "so much so that they could reduce you to mush in a singular attack" was in reference to this),. For 9-C, he is at least 1,090 Joules. Both of these values come from him scaling to, maybe even above Slappy.
 
Well the fight only works with 9-C so it's probably a good idea to assume that instead of automatically assuming that one that makes the fight unable to work.
 
Chucky doesn't have a clear Joule value unlike Mr. Wood, he is just vaguely 10-B (On the profile, it says that Chucky has 9-C durability, but the reasoning for it is bullshit) physically. Even if we assume he is the highest possible value for 10-B (106 Joules), in comparison to Mr. Wood's value of 1,090 Joules at minimum, he would still be 10.2 times stronger. For reference, our approximation for a one-shot difference is 7.5, and this is in the context of a 10-B fighting a 9-C, so it fits.

This is also ignoring the fact that he scales above characters who can do this, but that's its own kettle of spunk.
 
Even if Chucky did get his hands on a knife, he is fighting a living ventriloquist dummy. What exactly makes a knife stab so deadly is that they can damage organs or cause the victim to bleed out, both of which aren't things that would apply to a doll that isn't becoming more and more biological like Chucky.
 
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