ANSWERS: 1
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um... I can count at least three: The original time in "Death of Superman," again in the sequel, "Superman/Doomsday Hunter/Prey" and again in the horrible crossover "The Last Laugh" in a Superman tie-in issue. I know Doomsday has appeared at least three or four more times, but I don't remember if he actually ended up fighting Superman during those appearances.
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