PokéBase - Pokémon Q&A
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I have heard different numbers when it comes to this questions and so decided to ask it here.

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There are 19 Challange Medals. 17 relate to defeating the league with 1 type of pokmon, another relating to beating it with 1 Pokemon and the last being obtaining all the others.
There are also 7 Special Medals, 98 Adventure Medals, 56 Battle Medals and 75 Entertainment Medals which creates a total of 255 Medals.

Source: http://bulbapedia.bulbagarden.net/wiki/Medal

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I hate you for answering this question. You know that? xD JK.
brb I'm going to go cry in my dark corner
;~; D: :c

Not jks. :3
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There are 18 different Challenge Medals to be collected. There is a 19th one also under the 'Challenge Medal' category, but that one is only available once you get all the other Challenge Medals. xD

17 of these 18 medals are to beat the league with your party being only one particular type. The medal that is not part of these 17 is to try beat the league with only one Pokemon. And then, of course, there is the 19th one which is only obtained through collecting all the other Challenge Medals.

Hope I helped. :)
Sourcey Wource.

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