Merry Christmas and happy new year everyone!

Who will win?

I'm personally conflicted on the topic. Robocop's programming makes him infinitely more competent than the inspector, but Mr. Gadget sometimes gets out of trouble due to his clumsiness; the other 90% is Penny and Brain.

Well, initially Robocop would get the upper hand, but through the intervention of Penny he would get a chance to see his life in a new lighthearted perspective. AFter that he would clearly team up with Inspector Gadget to foil The Claw's latests dasterdly plot.

https://www.youtube.com/watch?v=zLjlnoAT_ns

After watching this, I will go for Robocop.

Robocop is inordinately more competent, but Inspect Gadget has a universe-bending knack of obliviously side-stepping any incoming threat and simultaneously causing his adversary to be placed in a very unfavorable situation. So long as Robocop is focused on Gadget himself, he'll keep inexplicably failing to do any real harm to the Inspector while the real threat (Penny) sets up to deliver the checkmate move from the sidelines.

Depends if it's purely 1vs1, or if Penny & Brain are helping Gadget...

1st case, I'd probably be a close 50/50 case, just to be decided by the fact whether or not Gadget's purerely insane luck (when it comes to avoiding harm without even realizing it) runs out.

2nd case would definitively be a win for Gadget, as Robocop would basically just wasting time with him while the real threat is completely unknown to him.

It would be a stalemate, as they are both good guys and have no reason to attack each-other.

However, morality aside, technically RoboCop would pull out his "Auto 9" handgun and destroy Inspector Gadget before he could say "Go-Go-Gadget Copter!"

However, moments before RoboCop pulled out his handgun the Inspector would spot a penny (lower case) on the ground, and "go-go-gadget supermagnet" to pick it up, sending RoboCop flying and flinging his gun away.

Don't know about Inspector Gadget (did he appear in any video games?), but Robocop's first game was a platformer in which he didn't have the ability to jump. (Fortunately, the sequel gave him that ability.)

He appeared in, 'Inspector Gadget and the Circus of Fear' for the Sinclair ZX Spectrum in 1987. It was published by Melbourne House.

Hope we're not using the new Robocop for the fight.

It's pretty obvious that Robocop has a HUMONGOUS advantage, with Inspector Gadget needing Penny and Brain to assist him just to make sure he doesn't get himself killed. Without a shadow of a doubt, Robocop would win, but if you want to be more lighthearted with it, you could say that Penny somehow finds out away to deactivate him and has Brain do it while he's busy shooting everything he's got at Gadget, who, by some miraculous cartoon logic, manages to accidentally avoid everything.

Under normal circumstances: Robocop.

However, if it's Terminator-mode Gadget from Robot Chicken, that would level the playing field.

Gadget's ability to accidentally avoid all danger is so consistent that it basically is one of his powers that must be accounted for in this analysis. Any direct attack against Gadget will fail due to an apparent happenstance every time, and while Gadget will also fail either due to his own incompetence or a gadget malfunctioning it will never be in such a way that causes him material harm.

As presented, Inspect Gadget is functionally a supernatural foe with reality-bending power. Unless he's up against an opponent who is also supernatural, or is so powerful as to win in spite of every happenstance possible conspiring in Gadget's favor, he's basically untouchable. Gadget would essentially be a Jar Jar Binks -esque character in any other setting; utterly infuriating for how he effortlessly and obliviously defeats far more skilled and competent foes because the universe is conspiring to ensure no harm can come to him.

In that case, Robocop could hold Penny/Brain hostage until Gadget just gives up.
Really, the basis of what direction this fight goes in depends mainly on who's world we're working with, Gadget's or Robocop's. If It's Gadget's universe of cartoon physics, he might win since anything can happen. If it's Robocop's gritty, more realistic world where he's used to taking down the toughest of criminals, he blows Gadget to pieces.

Gadgets wins. Both are good guys so they would not willingly attack each other, but Gadget's incompetence will create a dangerous situation where Robocop gets killed for sure.