Jeremy Rolleston began the sport of bobsleigh in 1999 after returning to Australiaa from playing professional rugby. His friend Kieran Hansen (short track speed skating 2002 bronze medallist) suggested he give the sport a try. He competed first as a brakeman, competing alongside Eill Alstergren in the lead-up to the 2002 Salt Lake City Games. After missing out on selected for the Games, Rolleston decided to try driving instead. In his first year as a pilot he qualified for the Games in Torino, 2006, an impressive effort, winning the Challenge Cup in Koniggsee, Germany along the way and equalling Australia's best ever Olympic result of 22nd in the 2-man sled. He produced consistently good results in the 2009/10 season, helping Australia to qualify two 2-man crews. In his second Games at Vancouver in 2010, Rolleston qualified as pilot for the two-man and four-man crews however the results at the Games were disappointing for him. In the first run of the two-man event, Rolleston and his pusher Duncan Pugh crashed. In something of a freak occurrence, Rolleston caught his foot in his steering mechanism as he climbed into the sled at the start of his first run, and was forced to firstly extricate himself and then reach down into the front of the sled to find the D-ring so he could steer. He had only just secured it when the sled tipped over, in curve four (of 16), leaving Rolleston and Pugh no option but to tuck themselves in as tightly as possible while the overturned craft slid down the remainder of the course. As they did not finish the course they were eliminated from further runs. The four-man sled withdrew because of injury.