Murkrow is a pretty tricky pokemon and he’s someone that shouldn’t be underestimated. While he could take down many fighters, he’s just not at Ash’s level. Ash has his Pikachu at the ready and one good thunder attack should be enough to win this round. Murkrow is strong, but he lacks the endurance that he would need to endure such an attack. Ash wins.
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.
Red and Ash are both pretty similar characters in concept, but their character personalities do tend to differ. Ash is a pretty happy trainer, but his Pokemon knowledge tends to evaporate over time. (Unova) His strategies aren’t the best, but his Pokemon do the best that they can. Red is pretty intense and he became the Pokemon Master. That’s something that Ash has always wanted to do, but he never could. Still, thanks to all of the various anime, Ash has enough pokemon to win this battle. Ash wins.
Update. Thanks to the Pokemon Origins special (Which I recommend), Red now has enough pokemon to completely destroy Ash. He has Mewtwo, Jolteon, Pikachu, and dozens of others at his disposal. I don’t really think that Ash has a chance anymore. Not even Pikachu can defeat an entire army! Red wins.
Charmaine may not be known as a pokemon fighter, but I’m sure that she could battle with the best of them if she needed too. Of course, Ash has his Pikachu at the ready. One good Volt Tackle would be enough to win Ash the match. At this point, he’s just grown to be too powerful. Ash has already passed 200 battles, maybe he will reach 300 soon! Ash wins.
This could be a tougher match than it would first appear. Ephraim crushed (Well…defeated) Ash when they fought in the tournament. Ash still had a ways to go and he made some key mistakes. If they were to have a rematch, I’m confident that Ash would win this time. Skiploom won’t be able to stop the mighty Bulbasaur! Ash wins.
Zachary Evans isn’t a very skilled trainer, but he can run pretty quickly. While he wouldn’t be able to evade Ash for long, he could give him a good race. After that, Ash could win with his Totodile. One good water blast is all he needs to end the round. Zachary Evans has lost his first match, but he gave it his all. Ash wins.
Tokichi is a pretty skilled trainer and there are few who can defeat him. He knows when it’s time to make the ultimate sacrifice and he always fights with honor. While that is all good, he still won’t be a match for a fighter as skilled as Ash. Ash will never back down from a fight and he rarely loses one. Ash wins.
Ledian is a strong pokemon, but no single pokemon seems to be a match for Ash. Ash has a lot of pokeballs at the ready which he can use to drain Ledian’s health. He also has a lot of pokemon at his disposal, including Noctowl. Ledian won’t be able to defeat such a large pokemon army. Ash wins.
Benji is part of the mountain patrol so he’s ready for just about any dangerous situation. Unfortunately, he’s never had to battle someone as powerful as Ash. In a one on one fight, Ash’s Pikachu would quickly take down Benji’s Ledian. Benji’s not quite as experienced as Ash Ketchum is. Ash wins.
Old Man Shuckle is a pretty smart guy and he’s also been around for a long time. Still, that won’t be enough to stop Ash and his many pokemon. One good blast from Pikachu and Old Man Shuckle will be down for the count. He’s never battled anyone as strong as Ash before and it would be a quick loss. Ash wins.