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Before I lost all of them only once for Pearl (it was my main game it's all my pokes before it got chewed up :( ), and twice on my Platinum which I lost while moving.
Pearl and Platinum are the original save files. I replayed Diamond a few times to get a Turtwig or for entertainment. I don't intend to restart any versions since I used them for breeding/trading.
I've never actually replayed my Diamond version, because I migrated all my Pokes from my Game Boy Advanced Games and didn't want to lose them. :P I kinda always wanted to restart because I forgot the storyline, but I just didn't want to lose all my friends from previous generations.
Yes I have played D/P/Pt multiple times. Usually I play it again to train different Pokemon or play a Nuzlocke or Monotype for fun. I remember one time I caught a shiny Sneasel on Pearl. So sad when the game stopped working. Now I play Platinum and currently I am doing an all Fighting Monotype.