I must side with Digimon in this comparison. Pokémon in both the games and anime(if it can be called such) is far too repetitive. The main series of games can basically be summed up as 'O hai there, we added more mons to the exact same plotline has before. Have fun paying to play a spruced up version of the same game'. I've lost all patience with that series. Digimon however, buying a different game actually lives up to the feeling of being a different game.

Anime wise I'd say comparing the two is a joke, Digimon proves superior by a landslide. Part of this is personal preference to the monsters themselves. On this front Digimon wins my heart my providing creatures that live up to the word 'monster', both in appearance and in spirit... While even the few Pokémon that should be legitimately scary still remind me of a plush toy.