The Winter Challenge is a Listed race run under Handicap conditions for open class horses conducted by the Australian Turf Club.

The Winter Challenge is run over 1500m and is the last black type race of the season in Sydney.

It was first run in 2011 and won by Foreteller.

The 2012 running of the Winter Challenge was over a mile at Warwick Farm but those since have been 1500m at Rosehill before being scheduled to be run at Randwick in 2022. However that meeting was abandoned and the race was run a week later at Rosehill.

Following his Winter Challenge victory in 2014, He's Your Man won the G1 Epsom Handicap three runs later.

Chris Waller has won 7 of the 13 runnings of the race but most for the jockeys is Jason Collett with three.

Mugatoo won carrying 57.5kg. Since this win he took out a Premiers Cup, Newcastle Cup, was 4th in a Cox Plate and won the All-Star Mile at Moonee Valley too.

The 2023 Winter Challenge was run for prizemoney of $160,000.

Notable winners of the Winter Challenge include Foreteller (2011), Coup Ay Tee (2013), He's Your Man (2014), Mister Sea Wolf (2018), Mugatoo (2020), Cross Talk (2022) and Barbie's Fox (2023).

The 2023 Winter Challenge was won by Barbie's Fox from Hosier and Steely.