Henshaw made his debut in the Freestyle Skiing World Cup in January 2006 in Les Contamines and finished seventh on the halfpipe. Since the 2008/09 season he has been participating in competitions on the AFP World Tour. In August 2008 he won his first win at the New Zealand Freeski Open in Wanaka . Also that season he won Big Air at the Jon Olsson Invitational in Åre and took second place at the Sweet Rumble in Trysil . In the 2009/10 season he won Big Air at the London Freeze, the Barcelona Big Air and the Frostgun Invitational in Val Thorens . He took second place in slopestyle at the Austrian Freeski Open in Kaprun and at the Jon Olsson Invitational in Åre. He finished the season in second place in the AFP Big Air ranking. At the beginning of the 2010/11 season he won the New Zealand Freeski Open in Cardrona . Another win at the Frostgun Invitational in Val Thorens followed that season. In January 2011 he won the silver medal in Slopestyle at the Winter X Games in Aspen . At the following Freestyle Skiing World Championships in 2011 in Park City , he won bronze in slopestyle. At the end of the season he reached second place in the AFP Slopestyle classification. At the beginning of the 2012/13 season he won in slopestyle at the New Zealand Freeski Open in Cardrona and in Big Air at the One Hit Wonder Down Under in Thredbo . In the further course of the season, another victory in slopestyle followed at the Winter Dew Tour in Breckenridge and a second place at the World Cup and US Grand Pix in Copper Mountain . At the Freestyle Skiing World Championships in 2013 in Voss , he came in 15th place in slopestyle. He finished the season in sixth place in the AFP overall standings and second in the AFP Slopestyle standings. In the 2013/14 season he finished third at the World Cup in Cardrona and in Copper Mountain and thus reached fifth place in the Slopestyle World Cup. In his first Olympic participation in Sochi in 2014 , he finished eighth in the first-ever slopestyle competition. In January 2015 he won the silver medal in Slopestyle at the Freestyle Skiing World Championships on Kreischberg . In January 2017 he was third in the World Cup on the Alpe di Siusi . At the Freestyle Skiing World Championships 2017 in Sierra Nevada , he finished eighth in Slopestyle.