cc @pieterpie
I’m in the middle of writing a blog entry about the 2009 Design Contest and currently have 7 of the 13 magazines en route to the UK from Japan. I’m hoping they give more information.
You’re right that the official announcement on the Pokémon Japan website claimed that each winner would receive 100 copies of their design as a card, but they also claimed that the contest spanned 12 magazines and that each runner-up would receive their design as a jumbo card - not only was there a 13th magazine (Shōnen Sunday), but none of these jumbo cards are known to have ever surfaced and I’d speculate that they were not awarded. Furthermore when these cards appeared for sale they almost always appeared as full sets, not as individual cards.
I’ve made some charts for my blog post comparing the PSA population of the 2009 and 2010 contests and the 2015 Art Academy release, which in my mind paint a pretty compelling picture that each winner did not receive 100 of their own design and very likely also did not receive double figures of the full set like the 2010 contest:
- 2015 Art Academy - each winner received 100 of their winning designs

- 2010 Pokémon Card Design Contest - each winner received 100 of their winning designs

- 2009 Pokémon Card Design Contest - each winner supposedly received 100 of their winning designs

The 2015 Art Academy has staggered and non-uniform distribution of graded cards as would be expected from each winner only receiving their own design and nothing more. The 2009 and 2010 contests however have a uniform distribution (albeit a very small sample size for 2009) which is not in line with what would likely happen if each winner received only their own design.
I’m hoping the magazines I have coming from Japan paint a much better picture.
I’ve pre-emptively concluded my upcoming blog post with the following:
Watch this space, I guess.