Glen Boss attended
Caboolture State High School from 1983 to 1985 where his strengths were rugby
league, playing as a hard-tackling fullback, and long distance running where he
came third in the State Championships.
Glen had been introduced to horses at an early age, and was a successful
Pony Club participant. However, at the
age of fifteen, a chance visit to the Gympie races with his grandmother,
introduced him to the magic of horse-racing and his future was sealed. His
apprenticeship as a jockey began in Gympie, and he learned to race on the bush
circuit of south-east Queensland, before moving to the Gold Coast and then to
Sydney in 1995, rising through the ranks to become one of the best jockeys that
Australia has seen.
A race fall in Macau in
2002 caused serious spinal injuries, but Glen fought back to win just about
every major race in Australia including the Cox Plate (3 times), the Golden
Slipper (twice) and the Doncaster Mile (6 times). Glen is regarded as a big-race rider and
became a favourite of punters as they knew that he would give an outsider as
much chance as a favourite. However,
Glen is probably best known for famously partnering the mare, Makybe Diva, to
three successive Melbourne Cups between 2003 and 2005, the only jockey in
Australian racing history to have achieved this honour.
At the 2010 Victorian
Thoroughbred Racing Awards, Glen won the Scobie Breasley Medal which recognises
jockeys who have achieved excellence in race riding. Having over 1,800 career victories, 2015 saw
Glen inducted into the Australian Racing Hall of Fame. He has ridden successfully throughout Asia
and now lives in Singapore with his family.
Glen still rides for the same reason that he first started as a 15 year
old – a love of horses.