Ash and Gary will forever be known as one of the greatest match ups in anime history. These guys never give an inch to the opponent and fight as if their lives depend on it! Gary has some extremely impressive pokemon like Nidoking/Nidoqueen, Umbreon, and Electivire. Electivire actually defeated Pikachu who is known as one of the strongest pokemon of all time! I’m not sure if I really buy that, but it was definitely an impressive feat. Ash has his Charizard, Sceptile, and Pikachu to counter this. Those are definitely his heavyweights and they can take on many opponents. In the end it comes down to the old quantity vs quality debate. (With the exception of the 3 pokemon that I mentioned) I think Ash will be able to pull ahead, but it will be a Very close battle. One that would keep on going until the very end! Ash wins.