DK Vs Bowser
Movie canon aside, with proper prep time, I do believe Donkey Kong could potentially win, the ONLY reason Bowser would eventually get the upper hand is simply because Bowser is ridiculously OP.
Outside of his fire breath and strength, he literally has dark magic that he can pretty much use at any time if he wanted, but he’s surprisingly a good sport and would rather use his pure koopa muscles to win the day instead.
So at best, DK could win if he dodges Bowser’s fire breath and fists along with his shell, which he’s pretty good at doing since his arch nemesis is a big crocodile with MULTIPLE alter egos.