Seabiscuit? While he was recovering from his bowed tendon, he covered mares at his owner's ranch, then came back and won the Santa Anita H.
In more recent times, one of my favorites Silveyville, winner of the G1 Hollywood Derby at 3 in 1981. For a couple of years in the latter part of his career, he would serve his mares in the spring, then come back to racing in the fall, going back to the farm after a couple of races at Santa Anita in the winter. The last year he ran, when he was 8, he won a G3 in January, then came back in late summer to run third in the Carleton F. Burke (G2) at Oak Tree and 2nd in the Citation H (G3) at Hollywood.
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