At the age of 15, Wiles began to participate in FIS races and national junior races from March 2008 . A specialization in the fast disciplines became apparent early on. Her first appearances in the Nor-Am Cup followed in December 2009, and her first victory in an FIS race was achieved in January 2010. She achieved her first point win in the Nor-Am Cup in November 2010, and began in the 2011/12 season to gradually establish itself in this continental racing series with several top 10 placements. With one win, three second and two third places, she finished second in the overall standings and the downhill standings of the Nor-Am season 2012/13 , while she won the Super-G standings. In addition, she won the US downhill championship title, albeit in the absence of the strongest runners.
Wiles made her debut in the World Cup on November 29, 2013 in the downhill from Beaver Creek , where she finished 43rd. Two weeks later she successfully defended her championship title. She won World Cup points for the first time on January 24, 2014, when she finished 15th on the downhill run from Cortina d'Ampezzo . In the two winters that followed, she was only able to classify herself sporadically in the points. On December 4, 2016, she achieved her first top 10 result in the Lake Louise descent . Five weeks later, on January 15, 2017, she finished third on the downhill run from Zauchensee , thus achieving her first World Cup podium.
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