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I don't think we can really say. The rules for all the leagues seem to be more or less the same, making the participants the only real variable. If you go to a Pokemon League and are unlucky enough to be put up against the guy who brought a Darkrai with him, for example, then that League's going to seem the toughest. But if you have to face the kid with a grass snake? Probably not so tough.
I dunno. It depends on the kinds of opponents you face. Not every one has to be like what Ash faced in that particular one. It's even possible they alter the rules according to how many participants there are so that the elimination process will be more efficient. If there's a low enough amount, they skip it entirely like with Sinnoh. I see nothing more difficult about the different situations, as they all involve one on one or three on three before going to the full battles. The only thing I see is that Johto perhaps is more forgiving with the Round Robin thing, since you can lose and still come out of it if you did better than the others in the group. (assuming Johto is the only one that does that, and is not one of the measures for a lot of participants above) The only "league" that is for certain more simple than the others is Orange. All you have to do is get the badges and you automatically face the Champion. This is why I'm not fully comfortable with calling it a real league, as it sounds more like a challenge than a proper league. This is also why this achievement is not looked on so highly by anyone. To even consider it equal to the other leagues is folly, regardless of what it's official standing is. As for what Ash himself faced, Sinnoh is obviously the hardest, with Hoenn being the second, although far off from what Sinnoh was.
The only "league" that is for certain more simple than the others is Orange. All you have to do is get the badges and you automatically face the Champion. This is why I'm not fully comfortable with calling it a real league, as it sounds more like a challenge than a proper league. This is also why this achievement is not looked on so highly by anyone. To even consider it equal to the other leagues is folly, regardless of what it's official standing is.
As for what Ash himself faced, Sinnoh is obviously the hardest, with Hoenn being the second, although far off from what Sinnoh was.
It would have to be one that was straight knock out rounds, ie if you lose your out of the comp. So that takes Johto out of the equation since it had pool match ups. Then I thought the most challenging matches to win are 6 v 6 and Hoenn started them with the top 32 rounds. So you'd have to get to the top 32 then win 5 6 v 6's in a row in order to win the whole thing. But It all really comes down to who you have on your team and who else is in the tournament and who the match ups are. In those respects Id say Sinnoh was the hardest from what we've seen so far.
I voted Hoenn, from the point of view of a random trainer coming in and seeing what needs to be accomplished in order to win. But at the same time those may have only been the rules for that particular tournament because of the amount of entry's they got that year or whatever. There's too many variables to say for sure
It would have to be one that was straight knock out rounds, ie if you lose your out of the comp. So that takes Johto out of the equation since it had pool match ups. Then I thought the most challenging matches to win are 6 v 6 and Hoenn started them with the top 32 rounds. So you'd have to get to the top 32 then win 5 6 v 6's in a row in order to win the whole thing. But It all really comes down to who you have on your team and who else is in the tournament and who the match ups are. In those respects Id say Sinnoh was the hardest from what we've seen so far.
I voted Hoenn, from the point of view of a random trainer coming in and seeing what needs to be accomplished in order to win. But at the same time those may have only been the rules for that particular tournament because of the amount of entry's they got that year or whatever. There's too many variables to say for sure
I've voted for the indigo Plateau because of two things 1st tough rules and regulations and 2nd you wave to win 8 rounds to win the whole shooting match and if you lose in the top 4 there's the bronze final (3rd place playoff)