In the games, Ash wouldn't stand a chance. In the anime, he has the advantage of being, well Ash, so I'd probably lose on some technicality or off the wall strategy that wouldn't work anywhere else.
Just as i would beat yugi in his show i would crush ash(a lot easier too) in pokemon. As well as using unevolved pokemon he is a moron. he made his pikachu use iron tail on an empoleon, just because pikachu always has to use iron tail. enjoy your 25 power move with 75% accuracy.(as opposed to the near 300 damage to be inflicted with a simple thunderbolt.)
I would beat ash with a smeargle and a magikarp
In the games, Ash wouldn't stand a chance. In the anime, he has the advantage of being, well Ash, so I'd probably lose on some technicality or off the wall strategy that wouldn't work anywhere else.