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Pokemon Diamond.

My game clock literally maxed out at 999:99 and wouldn't go any higher. The funny thing is, I've played much more than what the game clock showed. I REGRET NOTHING!!!

This may have also been the case for some other pokemon games in the past, like Pokemon Gold and Ruby, but I don't have those cartridges anymore. They were probably also maxed out. If not, very close to being maxed out to 999:99.