Simpson then moved to the two-man Star class, partnering lifelong friend Iain Percy; they won a bronze medal at the 2007 ISAF Sailing World Championships in Cascais to qualify for the 2008 Summer Olympics. The pair won the gold medal in Beijing in the Star class. After winning the Olympic gold, Percy and Simpson took a break from Star sailing and were in the TeamORIGIN afterguard for the 2010 America's Cup. In 2010, he and Percy won the Star World Championships in Rio de Janeiro.