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I only trained Pokemon up to 100 once in Pokemon Yellow. The rest were through cheats so I guess that doesn't count. In Yellow I had Pikachu, Venomoth, and Mewtwo at Lv.100.
I only have 2 100s. After I got an AR with 999 rare candies, i raised a magicarp aaaaaalllll the way up to 100. (i was curious.) IT SUCKED. It hardly beat a lv.30 something Peliper. My other one was a Jirachi. I traded my Dialga for it over WiFi.
MIne was my Torterra but all the rest were on LV 70 to 80 because 80 is usually as high as i raise them but my torterra is special so he is the only one that is on Lv 100 but my 1st real team on Lv 100 were
Tyfloshion (how ever you spell it)
Feraligatr
Maganium
Ariados (i know it is crap but it was so cool)
Blissy
Poliswine
Ariados Rocks by the way
Pokémon Ruby: Pelipper 0.0
Pokémon Diamond: Espeon - Interesting I haven't a single Lv.100 which is originally off my Diamond version, and as I tranfered them from my Emerald before they reached Lv.100 I have none on that game currently.
I have to confess that I have never actually trained any pokemon to level 100. The closest ones are in my team in Crystal, who are about 80 lv. I haven't played any of the newer games so much that I would be even close to levels that high. ^^"