Glen Boss

Glen Boss (Bossy) is one of Australia’s most accomplished and successful jockeys. Born in Beaudesert, Glen was raised on his family’s cattle property in Caboolture. After leaving school at 15 to pursue a riding apprenticeship, he achieved exemplary results in his early riding years in Brisbane before relocating to Sydney in 1994 where his career flourished.

Bossy has since gone on to win 96 races at Group 1 level, highlighted by 3 x consecutive Melbourne Cup victories on the legendary Makybe Diva in 2003/04/05 as well as 4 x victories in the Cox Plate and 2 x wins in the Golden Slipper (3 of the 4 legs of Australian racings Grand Slam).

Glen was an inductee into the Australian Racing Hall of Fame in 2015 and upon his return from riding in Singapore to Australia in 2019, he once again highlighted his position as one of the all-time greats of Australian racing with victories in iconic events such as The Everest (2019), The Golden Eagle (2019), Cox Plate (2020), and George Ryder Stakes (2021).

Following his retirement from professional riding in November 2021, Glen has filled obligations in the media as a content contributor for Entain Group through its wagering partner Ladbrokes, as well as being a key commentator on the free to air Channel 10 coverage of the 2023 Melbourne Cup Carnival.

Glen Boss’s legacy continues to grow, and his name remains synonymous with Australian horse racing’s greatest moments. He is an accomplished guest speaker and makes regular appearances at major events as a celebrity panellist and / or host to help create a lasting impact on the audience through his star presence.