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The first season's winner was Bill Rancic.Season 2: Kelly PerdewSeason 3: Kendra ToddSeason 4: Randal PinkettSeason 5: Sean YazbeckSeason 6: Stefanie SchaefferSeason 7: Piers MorganSeason 8: Joan RiversSeason 9: Bret MichaelsSeason 10: Brandy KuentzelSeason 11: John RichSeason 12: Arsenio HallSeason 13: Trace AdkinsSeason 14: Leeza Gibbons
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