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5 Dark Star
Kentucky Derby, 1953
The front-running 25--1 shot was an afterthought to undefeated Native Dancer. But the favorite was roughed up around the first turn and came up just a head short in the Derby's biggest upset—and the only loss of his brilliant 22-race career.
4 Sunday Silence
Preakness Stakes, 1989
The surprise victor in Louisville went off as the second choice in Baltimore to Easy Goer, who seized the lead with a half mile to go—only to have Sunday Silence take it back coming out of the clubhouse turn. The two colts stared each other in the eye for more than a quarter mile before the gutsy bay won by a nose.
3 Winning Colors
Kentucky Derby, 1988
In the most acclaimed victory of trainer D. Wayne Lukas's Hall of Fame career, the third and last filly to win the Run for the Roses stole the race on the lead, holding off Forty Niner by a neck.