I believe the horse known as John Henry has 39 documented wins, and by far is the horse with the most race wins.
Kingston won 89 races when he retired at age 10 in 1894. That's the record to this day.
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I think Willie Shumaker holds the record for most wins. Not only was he a brilliant jockey but he had one of the longest careers in history. It's a dangerous line of work and most leave the profession much sooner than Willie did. Many can't continue to ride due to injuries sustained from their riding fractious Thoroughbreds at breakneck speeds.