In addition to junior races , Bennett first took part in FIS races in 2007 . The first starts in the Nor-Am Cup in February 2009 were followed by victory in giant slalom and second place in slalom at the US junior championships next month. Bennett has been regularly competing in the Nor-Am Cup since February 2010, and on February 21, 2010, when he finished sixth in the Super Combined in Aspen, he achieved his first top 10 result in this racing series. After finishing in the top 10 of a Nor-Am race just one more time in the next 23 months, but taking several podiums in FIS races, Bennett celebrated his first on February 9, 2012 in the Aspen Super-G Victory in the Nor-Am Cup. The following day he was on the podium again in the second Super-G in Aspen, second behind Jeffrey Frisch . He finished fourth in the 2011/12 Super-G classification . In 2012, Bennett took part in a Junior World Championship for the only time in Roccaraso, Italy.
In the 2012/13 season of the Nor-Am Cup, he finished third in the downhill classification, which enabled him to have a fixed starting position in the World Cup . The World Cup debut took place on December 1, 2013 in the downhill from Lake Louise , which he finished in 64th place. With several podium places, he secured first place in the Nor-Am downhill classification in the 2013/14 season . In the winter of 2014/15 Bennett competed in ten World Cup races, but could not classify himself in the points once. He scored World Cup points for the first time on December 4, 2015 with 29th place in the downhill from Beaver Creek . Two weeks later, on December 19, 2015, he surprised everyone with 6th place in the downhill run from Val Gardena (after only finishing 48th the day before). Another top 10 result followed on January 22nd, 2016 in the combination of Kitzbühel . He also achieved two top 10 results in winter 2016/17.
His best result so far is 4th place in the downhill from Val Gardena on December 15, 2018. He repeated this 13 days later in the downhill from Bormio .