He umpired in the minor leagues from 1982 to 1989 before joining the NL's regular staff in 1990. Winters has worn uniform number 33 his entire career. He has officiated the All-Star Game in 1995, 2007, 2010, and 2016, the Division Series in 1998, 1999, 2000, 2001, 2002, 2006, 2010, 2013, 2014, 2015, and 2018, the League Championship Series in 1997, 2004, 2008, 2011, and 2012, and the 2002, 2006, 2010, and 2015 World Series. He was crew chief for the Division Series in 1998, 1999, 2014, and 2018.