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Originally Posted by King Glorious
As far as I can tell, it's happened four times.
1980, Oaks winner Bold N Determined beat Derby winner Genuine Risk in the Maskette by a nose.
1988, Derby winner Winning Colors beat Oaks winner Goodby Halo by 1/2 length in the BC Distaff (both behind Personal Ensign). Goodbye Halo and Winning Colors had traded victories prior to them winning the Derby and Oaks.
1999, Derby winner Charismatic beat Oaks winner Silverbulletday in the Belmont although neither won the race.
2009, Oaks winner Rachel Alexandra beat Derby winner Mine that Bird by a length in the Preakness.
Even though it wasn't Derby vs. Oaks, I'd throw in Oaks winner Rags to Riches beating Preakness winner Curlin by a nose in the 2007 Belmont. That's a very good record right there. Am I missing any other times when it's happened?
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Princess Doreen got beat by Zev in the '20s.
Cicada was defeated by Belmont winner Jaipur (plus Derby/Preakness-placed Ridan) in '62 Travers.
Davona Dale got lit up by Derby runner-up General Assembly in the '79 Travers.
Lite Light was behind Derby runner-up Best Pal in the '91 Super Derby.