In the 1992 Barcelona Games, he won a gold medal in the men's long jump C7–8, for which he received a Medal of the Order of Australia. He also competed in the men's 100 m, 200 m and 400 m C8 events. Thrupp followed this up in the 1996 Atlanta Games with a men's long jump F34–37 gold and a bronze in the 200 m T37. In 2000, he received an Australian Sports Medal. That year, in the 2000 Sydney Paralympics, he was a part of the winning men's 4x100 m and 4x400 m T35–38 relay teams. At these Games, he also competed in the men's 100 m, 200 m and 400 m T38 events. At the 2004 Athens Games, he won gold in the men's 4x100 m T35–38 and bronze medals in the men's 100 m T37 and long jump T36–38. His sixth appearance in the 2008 Beijing Games led to a third successive men's 4x100 m relay gold medal. He also competed in the men's 100 m T37 and men's long jump F37/38.