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Derek Jeter won his five Gold Glove Awards in 2004, 2005, 2006, 2009 and 2010.
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By the look of it 1957 the first awards were handed out! http://en.wikipedia.org/wiki/Rawlings_Gold_Glove_Award
11 ... he won the Gold Glove each season between 1978-1988.
Don Mattingly won nine Gold Glove awards, the most in Yankees history.