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Originally Posted by Port Conway Lane
Good question. I think it happens most often in restricted 2yo state bred stakes, less often in open stakes and must be rare in graded stakes.
Two names struck me when I saw your question. In Alydar's first start (as the favorite) he was defeated by Affirmed in a stakes race.
A more obscure filly I recall was Masked Barb winning a resricted stakes in the mid 80's. The memory is clouded a bit but I think she was trained by Bernie Bond who was practically unbeatable in juvenile races. I'd bet a dime to a dollar Bond sent out more than a handful of fts stakes winners in the 80's but can't recall the other names. Masked Barb stood out because she paid double digits.
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Didn't know any of this so thank you!