The Sydney City2Surf has been held as an annual event since the first run on September 5, 1971. It was conceived by the staff of The Sun (now The Sun-Herald) and inspired by the Bay to Breakers event in San Francisco. Approximately 2000 people competed in the first event. Since 1973 it has been held on the second Sunday in August, except for the race held in 2000, moved to July due to the Sydney Olympics in August.
In recent years, over 60 000 people have entered the annual 14km Sydney race, which has become the largest timed running race in Australia. It is still primarily sponsored and organised by The Sun-Herald. As of 2008, the course starts in four groups. Runners expected to complete the course in under 75 minutes are in the first group and runners expected to complete in under 100 minutes in the second group. Other entrants may select between a third runners group and the fourth "Back of the Pack" group if walking, using a wheelchair or pushing child strollers.
The route taken by the entrants passes through the suburbs of Kings Cross, Rushcutters Bay, Double Bay, Rose Bay, Vaucluse, Dover Heights and Bondi Beach. The most difficult part of the course is "Heartbreak Hill" at the halfway mark, a 2km long steep ascent from Rose Bay to Vaucluse along New South Head Road.
The course record is 40:03, set by Steve Moneghetti in 1991. The women's record is 45:08 minutes, set by Susie Power in 2001. Non-Australian athletes have typically won the race in recent years, including repeat winners Laban Chege (1999–2000), Patrick Nyangelo Lusato (2003–2005), and Dickson Marwa (2006–2007). In 2008, Martin Dent became the first Australian winner since Lee Troop in 1997. Marwa was competing in the 2008 Olympics.
Features en-route include many amateur bands performing along the suburban roads, and many City2Surf participants dressed in novelty themed costumes.
| Year | Name | Country | Time |
|---|---|---|---|
| 2008 | Martin Dent | 41' 12" | |
| 2007 | Dickson Marwa | 41' 10" | |
| 2006 | Dickson Marwa | 40' 49" | |
| 2005 | Patrick Nyangelo Lusato | 41' 12" | |
| 2004 | Patrick Nyangelo Lusato | 41' 04" | |
| 2003 | Patrick Nyangelo Lusato | 41' 55" | |
| 2002 | Jussi Utrianen | 41' 37" | |
| 2001 | John Msuri | 40' 24" | |
| 2000 | Laban Chege | 40' 25" | |
| 1999 | Laban Chege | 40' 27" | |
| 1998 | Daniel Browne | 41' 35" | |
| 1997 | Lee Troop | 40' 55" | |
| 1996 | John Morepedi | 40' 19" | |
| 1995 | John Morepedi | 41' 05" |
| Year | Name | Country | Time |
|---|---|---|---|
| 2008 | Rebecca Lowe | 47' 18" | |
| 2007 | Jessica Ruthe | 46' 33" | |
| 2006 | Anna Thompson | 47' 15" | |
| 2005 | Kerryn McCann | 46' 27" | |
| 2004 | Hayley McGregor | 46' 22" | |
| 2003 | Hayley McGregor | 47' 28" | |
| 2002 | Susie Power | 45' 50" | |
| 2001 | Susie Power | 45' 08" | |
| 2000 | Susan Hobson | 48' 24" | |
| 1999 | Kylie Risk | 46' 25" | |
| 1998 | Kerryn McCann | 48' 10" | |
| 1997 | Elizabeth Miller | 47' 30" | |
| 1996 | Heather Turland | 46' 43" | |
| 1995 | Elizabeth Wilson | 47' 05" |
Deaths during the race have occurred several times. In both 2000 and 2008 a competitor died of a heart attack close to the finish line of the race. After the 2008 death medical academic Michael O'Rourke noted that a runner developing arrhythmia and cardiac arrest happens most years but that the sufferer is usually revived.
The course record is 35:24, set in 2006 by Brett Cartwright.