David Probert was born in Bargoed, Wales and attended Ysgol Gyfun Cwm Rhymni, a Welsh language school. Growing up, he competed in pony racing around Wales, before attending, the British Racing School in Newmarket, aged 16. 

After completing his course, Probert went to work at Andrew Balding’s Kingsclere yard. As an apprentice jockey and he rode his first winner in December 2007, when Mountain Pass won a race at Wolverhampton for Welsh trainer John Llewellyn. In 2008, he rode 50 winners and shared the British flat racing Champion Apprentice title with fellow Kingsclere apprentice William Buick. 

Probert enjoyed a standout 2014, becoming the youngest Welshman to ride in the Derby, claiming his first Royal Ascot winner and reaching 107 winners for the year. In April 2022, he was crowned all-weather champion jockey for the 2021/22 season. He then ended the 2022 Flat season by winning the Welsh Flat Racing Jockey of the Year award after recording five Group 2 victories.