The Challenge Stakes is a Group 2 race run under weight-for-age conditions by the Australian Turf Club that has been part of the Sydney racing calendar for more than 100 years.

The Challenge Stakes was first run in 1906 and is Sydney's most prestigious 1000m sprint race. Only once, in 2012 when run over 1100m at Rosehill, has the Challenge Stakes not been run over five furlongs or 1000m.

From 1906 to 2001 inclusive the Challenge Stakes was run at Randwick. From 2002 to 2006 the Challenge Stakes was run at Warwick Farm and has since been run at Randwick from 2007-2010, Rosehill in 2012, Warwick Farm in 2013 and Randwick since 2014.

The Challenge Stakes was run under handicap conditions from 1906 until 1979 when it became a weight-for-age event. The weight carrying record for the Challenge Stakes when a handicap was 10 stone three pounds (65kg) carried by The Hawk in 1925.

The Challenge Stakes was traditionally run in January and for many years was the feature race on Randwick's Australia Day program. Since 2003 the Challenge Stakes has been incorporated into the revamped Sydney autumn carnival agenda and serves as a key lead-up for sprinters preparing for the G1 Galaxy (1100m) and G1 TJ Smith Stakes (1200m).

There have been two triple winners of the Challenge Stakes. Razor Sharp won the Challenge Stakes in 1982, 1983 and 1984 and At Sea followed him in 1985, 1986 and 1987.

Another ten horses have won the Challenge Stakes twice – Golden Hop (1913/14), High Caste (1940/1942), Felbeam (1945/46), San Domenico (1949/50), Gay Gauntlet (1967/1969), Cangronde (1997/98), Star Of Florida (2003/04), English (2016/17), Eduardo (2021/22) and Passive Aggressive (2023/24).

Other notable winners of the Challenge Stakes include Caesar, Yaralla, True Leader, Tarien, Dubbo, Wenona Girl, Time And Tide, Zephyr Bay, Crimson Cloud, Snippets, Show County, Spanish Mix, Moss Rocket, Easy Rocking, Bomber Bill, Snitzel, Spark Of Life, Hay List, Rain Affair, Snitzerland, Miracles Of Life, Redzel and Nature Strip.

Only two horses have won the Challenge Stakes/Galaxy double (Playbill/Snippets) while Ab Initio and Nature Strip are the winners of the Challenge Stakes/TJ Smith Stakes double since the latter race was introduced in 1997.

The 2024 Challenge Stakes had prizemoney of $500,000.

The track record at Randwick was smashed in the Challenge Stakes by Eduardo in 2021 when he ran 55.20.

In 2022 there was only a field of four and it was expected the two previous winners Nature Strip and Eduardo would fight it out but a country horse Shelby Sixtysix charged home to just miss as the crowd roared.

The 2024 Challenge Stakes was won by Passive Aggressive from Zapateo and Aft Cabin.