Derek Jeter By Dahler25 Jun 26, 1974 Derek Jeter is born May 19, 1992 Derek Jeter is drafted May 29, 1995 Derek Jeter's Major League Debut Oct 26, 1996 Derek Jeter wins first World Series Nov 10, 1996 Derek Jeter gets Rookie of the Year award Nov 5, 1998 Gets Al All Star and New York Yankees POTY Awards Oct 20, 1999 WIns Second World Series Nov 4, 1999 Gets 2nd Al All Star and 2nd New York Yankees POTY Oct 18, 2000 Wins 3rd World Series Nov 5, 2000 Gets 2 MVP awards, Babe Ruth Award, 3rd AL All Star Award, and 3rd NYY POTY Award Nov 7, 2004 Wins First Gold Glove Award Nov 4, 2005 Wins 2nd Gold Glove award Nov 10, 2006 Wins First Silver Slugger Award and 3rd Gold Glove Award Nov 12, 2007 WIns 2nd Silver Slugger Award Nov 9, 2008 WIns 3rd Silver Slugger Award Oct 27, 2009 Wins 4th World Series Nov 11, 2009 Wins 4th Silver Slugger and 4th Gold Glove award Nov 4, 2010 Wins 5th Gold Glove Award Jul 9, 2011 3000th Hit Nov 3, 2012 Wins 5th Silver Slugger Award Nov 9, 2014 Retires with Most Hits Ever as a Shortstop