Gregg has mainly participated in the Nor-Am Cup and the US Super Tour since 2005. He has achieved 31 podium finishes so far, including nine wins (as of the end of the 2017/18 season). In the 2010/11 , 2011/12 , 2013/14 and 2016/17 seasons he finished third and in the 2009/10 season second in the overall ranking of the US Super Tour. In the 2017/18 season he came fourth in the overall ranking of the Nor-Am Cup. He ran his first World Cup race in January 2008 in Canmore , which he finished with 60th place in the sprint. At the 2010 World Cup finals in Falun , he came in 41st place. With the 32nd place in the pursuit race he reached his best place in the World Cup so far. At the 2014 Winter Olympics in Sochi , 46th place in the 30 km skiathlon was his best result.