The weirdest one I remember like that was with Willa On The Move.
Willa On The Move got a Grade 1 win in the 1988 Ashland and was 3rd in the Kentucky Oaks.
Willa On The Move - spelled exactly the same way but obviously a different horse - ran a distant 2nd to You in the Grade 1 Acorn than won a Graded Stake at Saratoga in the Honorable Miss.
In fact, Willa On The Move's dam is a half sibling to two Grade 1 winners .. one being Will's Way and the other being Willa On The Move.
When you think about it ... it's kind of weird saying Willa On The Move is a half sister to the mother of Willa On The Move.
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