Oakley participated mainly in the Nor-Am Cup from 2004 to 2011. She got two victories and won the overall Moguls ranking in the 2010/11 season. She made her debut in the Freestyle Skiing World Cup in March 2011 in Voss and finished 16th in the Dual-Moguls. At the beginning of the 2011/12 season she reached her first top ten placement in the World Cup in Méribel with sixth place in the Dual Moguls. Six top ten results followed in the further course of the season, including third place in Calgary and thus reached 26th place in the overall World Cup and ninth place in the Moguls World Cup at the end of the season. In March 2012 she became the American champion in the dual moguls discipline. In the following season she came in 12 World Cup starts, six times in the top ten and thus achieved 13th place in the Moguls World Cup. After finishing 21st and 11th at the beginning of the 2014/15 season, she won her first World Cup victory in the Moguls competition in Deer Valley . This was followed by three top ten results and at the end of the season 29th place in the overall World Cup and ninth place in the Moguls World Cup. At the season highlight of the 2015 Freestyle Skiing World Championships on Kreischberg , she took 18th place in the Moguls competition. In the 2016/17 season she achieved four top ten results in the World Cup and at the end of the season she was 16th in the Moguls World Cup.
Oakley has participated in 51 World Cups so far and has been in the top ten 22 times. (Status: end of season 2016/17)
United States