Held over 1,800 metres at Caulfield, the Underwood is one of the more interesting races during the spring carnival.

While usually being a great betting race, it also provides a useful form guide for the Caulfield Cup and Cox Plate. Indeed, many Caulfield Cup and Cox Plate aspirants use the Underwood as a lead-up race.

The irregular distance of 1,800 metres adds to the intrigue of the Underwood.

A furlong longer than a mile, but also shorter than a mile and a quarter, the 1,800 metre start at Caulfield allows for a fairly long straight run before the horses and their jockeys hit the first turn. Therefore, horses that have drawn a wide barrier have a good chance of finding a spot close to the rail, provided the breaks come their way.  

While the WFA race over 1,800 metres appears the natural lead-up race for the Cox Plate, the winner of the Underwood gains exemption from a ballot in the Caulfield Cup, which is run over 2,400 at the same track, typically three wakes later. Therefore, a dominant performance in the Underwood will often suggest that the horse has a good chance of running out the mile and a half of the Caulfield Cup.

A horse that made the Underwood his own was Ajax. This mighty stallion won back-to-back-to-back, taking out the 1938, 1939 and 1940 editions. Other Australian equine royalty including Phar Lap and Tobin Bronze have salted in the Underwood.