A legacy
of loyalty

Born in South Australia to a racing family; his father, Darren Holland, was also a successful jockey.

Made his professional riding debut at the age of 17 at Ceduna, South Australia.

Captured his first career victory at Ceduna, riding a horse named Brookman.

Established himself as a rising star by riding four consecutive winners aboard Jest For Fun during his apprenticeship.

2 (Australasian Oaks and Newmarket Handicap).

Achieved his first Group 1 victory in the Australasian Oaks at Morphettville, riding the filly Small Minds.

Won the Group 2 Adelaide Cup for the first time, guiding Tanby to victory.

Secured a second Adelaide Cup win aboard the promising stayer Surprise Baby.

Won the Group 3 Geelong Cup on Tralee Rose, a victory that holds special significance as it qualified the horse for the Melbourne Cup.

Reached a lifelong goal by competing in his first Melbourne Cup, finishing 9th aboard Tralee Rose.

1,080 victories across Australia.

Remembered as a "once in a lifetime person" and a devoted father to his four children: Harley, Luca, Frankie, and Lily.

Achieved his greatest career milestone by winning the Group 1 Newmarket Handicap at Flemington on In Secret. He took the ride as a last-minute replacement for Jamie Kah, earning widespread praise for his composure and subsequent humility.

Tragically passed away at the age of 34 following a race fall at Donald Racecourse in regional Victoria.

A public memorial and funeral service were held in the Flemington Mounting Yard, attended by thousands from the racing community to honor his life and legacy.

The Victoria Racing Club (VRC) inaugurated the Dean Holland Trophy, to be presented annually to the winning jockey of the Newmarket Handicap at Flemington as a permanent tribute.