opened the package for the first time, turns out I had 3 from 2010-2011
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BUMP! I should have done so a long time ago, but all the information provided by @hayo has been added, and instead of a display of pictures and some basic information, it’s now an actual article. I really want to thank Antoine for his huge contribution and added sources, distribution information, and release dates. 50% of this article is thanks to him; thanks a lot for sharing all this information! 
I’ve left a few red texts where information is still missing. If anyone has this information, or perhaps even knows about a Teach Set not yet part of this article, let me know. Oh, and if anyone has the Teach Set 2009 Pikachu to sell to me, I would love that even more. 
Thanks for reading! 
Greetz,
Quuador
Well done, @quuador! Congrats on making it an official article, even though it has always been the single best resource on the various Teach sets.
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Oh hey, I picked one of these posters up a few months ago and had no idea where it originated.
Not sure if it’s of much interest here, but I decided to take some higher quality scans of the front and back (note that it’s roughly A3 size so it’s split into 4 images instead of 2):
[SPOILER: Click to show](javascript:void(0);)**Spoiler: Much larger images (click to show)**Front left: i.imgur.com/MwSLU6z.jpg
Front right: i.imgur.com/mDLfLvD.jpg
Back left: i.imgur.com/qyqxfxP.jpg
Back right: i.imgur.com/SrUXKAg.jpg
Not that it means all that much, but the copyright date on this poster is ©1995-1999.
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Added both to the article, thanks!
Btw, I don’t see a Pichu in that poster, why do you even have it, haha? 
Greetz,
Quuador
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It actually came in a YJA listing which also had this strange double-sided checklist card which is about the size of a regular jumbo Pokémon card but perhaps ever so slightly thicker:
Would be cool to identify what it’s from, but I guess that’s something for a different thread.
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Asked a friend to translate the added text on the 2008 Teach Set Shaymin, and she provided me with translations. (I chose the Shaymin to get her interest, as it’s one of her favorite Pokemon.)
The text below the smaller card image, with the red box around it, is “Place two damage counters on the opponent.”
The text below the red box, and above the yellow circles, is “8 damage counters required to defeat.”
So nothing particularly interesting, but there you go.
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A bit late with my response, but I’ve added it to the article. Thanks! I think I read this at work, and forgot about it later on… But it’s added to the article now, so thanks for the help. 
Greetz,
Quuador
Bump. Now that I’ve acquired the Teach Set of 2009, I’ve been able to provide better pictures of those, and a side-by-side of the Pikachu of 2008 and 2009. I’m very happy to now have all four Pikachu Teach/Tryout Set cards in my collection (unless someone discovers a Teach/Tryout Set other than the six mentioned in the article containing a Pikachu). @japanime You don’t happen to know of any other Teach/Tryout Sets besides these six, right (please say no, haha)?
Greetz,
Quuador
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@nine posted this picture on Instagram a couple of days ago:
https://instagram.com/p/CIc-4kdljQg
I see it’s a CoroCoro Comic volume 5, but does anyone know from which year or has a picture of the front? And this CoroCoro Comic is the one that came with the Teach/Tryout Set from 2000 if I understand correctly, or it only mentions them and the actual source is from somewhere else? Sometimes I really wish I could read Japanese…
Greetz,
Quuador
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It’s not CoroCoro Comic but instead Shogakukan’s Kindergarten Magazine (幼稚園). “5月号” means it was the May issue (which would have likely been released in April). The presence of the Pikachu Movie 2000 stamp means it was either 1999 or 2000 - probably 2000.
I have a sealed copy of the April 2000 issue which also features a Pichu on its cover - I’ll have to keep my eyes peeled for this one to pop up.
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Awesome! Thanks for the info @nine, @majomaal, @pichufan I’ll update the article with the new information (soon).
Greetz,
Quuador
@quuador ,
The purpose of the text in the box is to restate the second move’s description but in a much more kid friendly manner using only kana which makes it a lot more digestible for younger kids. You can read 「」as quotation marks in English.
せつめい「でんげき」
Explanation “Thunder Jolt”
あいてに ダメージカウンターを3つのせる。コインをなげて「うら」なら じぶんにも ダメージカウンターを1つのせる。
Put 3 damage counters (on the enemy Pokemon). Flip a coin, if “tails”, attach 1 damage counter to yourself.
ダメージカウンター4こ のったら まけ
If you get 4 damage counters you lose. (See Pikachu’s 40HP)
I left out the furigana (the small letters above) because I can’t properly type them on my work computer and it’s just the hiragana versions of the katakana letters. Fun fact, since the Teach sets were made specifically for kids, it makes sense for hiragana to be included since that is what children learn to read first. Typically furigana is used for kanji pronunciation as adults should be able to read katakana
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This book is the May issue of Learning Kindergarten(学習幼稚園).
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I’ve updated the main article. Thanks again for all the info @majomaal, @pichufan, and @nine.
Greetz,
Quuador
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Bump. Huge thanks to @neos for providing pictures of the previously unknown magazine for the 2008 Teach/Tryout Set, for which we now know was released on July 31st, 2008 inside the Pokémon Fan Club Shogakukan Special volume 4 magazine.
Apart from the misplaced advertisement of Denny’s restaurant, I’m happy to say all the release information of all five Teach/Tryout Set cards is now complete in the article, little over three years after I started writing it.
Greetz,
Quuador
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I know I am replying to a very old article but this just came in super handy trying to identify a card I received in a lot. Thanks @Quuador !
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