Kammala wannan jumla: Ya yi aiki a cikin ƙananan ƙungiyoyi daga 1982 zuwa 1989 kafin ya shiga ma'aikatan NL na yau da kullum a 1990. Winters ya sa lambar rigar lamba 33 a duk aikinsa. Ya yi aiki a cikin All-Star Game a 1995, 2007, 2010, da 2016, da Division Series a 1998, 1999, 2000, 2001, 2002, 2006, 2010, 2013, 2014, 2015, da 2018, da League Championship Series a 1997,
2004, 2008, 2011, da 2012, da kuma 2002, 2006, 2010, da kuma 2015 Duniya Series. Ya kasance shugaban ma'aikata na Division Series a 1998, 1999, 2014, da 2018.