Ian Chesterman (born 17 April 1959) is a member of the Australian Olympic Committee and an Australian Winter Olympic administrator.
He has been the Chef de Mission (the head of the Australian delegation) at the 1998 Nagano, 2002 Salt Lake City and 2006 Torino, 2010 Vancouver and 2014 Sochi Olympic Winter Games. He was the General Manager at the 1994 Lillehammer Games, being Deputy to Geoff Henke.
Australia had broken new ground during Chesterman's time in the upper reaches of winter sports administration. In 1994, Australia's short track relay team won Australia's first Winter Olympic medal, a bronze.
At the 1998 Olympics in Nagano, to which Australia sent 24 athletes,Zali Steggall won the country's first individual medal with a bronze in slalom skiing.
At the start of the 2002 Olympics, Chesterman addressed the team and said "historically our winter teams have been the child racked by self-doubt, shy in nature as we saw our big brother, our summer Games team, take on and conquer the world." He added, "but over time we have developed a belief in ourselves".
In 2002, Australia won two gold medals, having never previously won an Olympic event. Australia’s maiden gold medal came in highly unlikely circumstances. Steven Bradbury, a member of the bronze-winning 1994 relay team, won gold in short track speed skating when all of his competitors in the 1,000 m final crashed out on the final turn while jostling for the medal positions.Alisa Camplin, who had never won a World Cup event, won the women's aerial skiing, after overtaking her rivals' points tally on the second and final jump.
In 2006 in Torino, Australia sent 40 athletes to compete in 10 sports, a record number of competitors and events, and Australian officials publicly declared their expectation of winning medals. Camplin won bronze, her second Olympic medal. Favourite Dale Begg-Smith won gold in moguls skiing.
In 2010 in Vancouver, Australia had its most successful Winter Games, winning two gold (Torah Bright in Snowboard Halfpipe and Lydia Lassila in Aerials Skiing) and one silver (Dale Begg-Smith in moguls).