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Originally Posted by King Glorious
Short list as I suspected. Which makes it not so unusual that there has been a long gap since the last time it was done.
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I only did 1940-1969 ... shall I go further?
How about Secretariat, Spectacular Bid, Pleasant Colony, Spend A Buck*, and the aforementioned Sunday Silence? All multiple Triple Crown race winners who won G1's over older horses.
That brings the total to 10.
*Spend A Buck won the Jersey Derby over other Triple Crown horses .. instead of the Preakness ... collecting a big bonus.