Just a random thought that crossed my mind today.
I think England would have a Jigglypuff, Clefairy, or some other fairy-like Pokémon, Italy would have a Skitty, America would have Pikachu or Charizard, Germany would have a Houndour... I haven't decided on anything farther than that. :P
I could see Russia with a Munna... Not sure why, but I could.
Russia would have a Froslass, being a Ghost-Ice type, Maybe Gengar, Sunflora, Glalie, Sableye, and Weavile as well.
America would have a Braviary. I know that for sure.
England would have a MagikarpCelebi, Alakazam, Shuppet, Jynx, Eevee, and maybe a Jirachi.
France would definitely have a Serperior and a Roserade.
China would have a Gyarados, Emboar and perhaps a Skitty.
Germany would have a Scizor, Conkeldurr, Zebstrika, and maybe as a starter, Blaziken.
Japan would have a Samurott, Gallade, and Medicham.
And for Italy, a Bidoof, Sentret, and Mew.
I've been *attempting* to write a Hetalia and Mystery Dungeon crossover, so here are the decisions I've made so far:
America - Braviary
England - Charizard
France - Ninetales
China - Mienshao
Russia - Weavile
Italy - Plusle
Romano - Minun
Japan - Lucario
I actually found a youtube video on this [APH] If Hetalia characters were Pokemon Trainers