Living in Somerby, England, the accomplished athlete, business owner, coach, and horse trainer has a rich history in equestrian sports. He first tried riding at age six in Culcairn, NSW, Australia. By the following year, he was competing on a horse borrowed from his uncle.

| Season | Event | Rank |
|---|---|---|
| 2021 | Team | S Silver |
| 2021 | Individual | B Bronze |
| 2012 | Team | 6 |
| 2012 | Individual | 13 |
| 2004 | Team | 6 |
| 2004 | Individual | 57 |
| 2000 | Team | G Gold |
| 2000 | Individual | S Silver |
| 1996 | Team | G Gold |
| 1996 | Individual | 11 |
| 1992 | Team | G Gold |
| 1988 | Team | 5 |
| 1988 | Individual | 8 |
| 1984 | Team | 5 |
| 1984 | Individual | 15 |
He is associated with Somerby Stables in England. Known as "Hoy Boy," he has made significant contributions to the sport.
One of his most memorable achievements is winning gold in the team event at the 2000 Olympic Games in Sydney. His wife Stefanie has been the most influential person in his career.
He looks up to Brazilian Formula One driver Ayrton Senna, Australian Moto GP rider Casey Stoner, and Australian road cyclist Cadel Evans.
His sporting philosophy revolves around working closely with each horse to understand their personality. He believes in doing a lot of work from the ground and different forms of cross-training for fitness. His goal is to achieve harmony with each horse.
He was the flag bearer for Australia at the opening ceremony of the 2018 World Equestrian Games in Tryon, NC, United States. He was inducted into the Equestrian Australia Hall of Fame in 2015 and Australia's Sporting Hall of Fame in 2001. He also carried the flag for Australia at the 1996 Olympic Games in Atlanta. In 1993, he received the Medal of the Order of Australia.
At the 2020 Olympic Games in Tokyo, he became the oldest athlete representing Australia to win a medal at age 62. He claimed bronze in the individual eventing competition and silver in the team competition. These Games marked his eighth appearance, setting a record for an Australian athlete from any sport.
His great-grandfather P.T. Heywood trained Artilleryman, the racehorse that won the Melbourne Cup in 1919.
He has lived in England since the 1990s. In December 2013, he moved to Somerby Stables in Leicestershire. The facility is designed for training students and hosting people who want to train with him.
In January 2020, he became an ambassador for the Equestrian Fire Relief Australia Fund. He expressed his concern about the devastating fires affecting his home country and aimed to provide financial and moral support through this campaign.
He resides with his wife Stefanie, daughter Philippa (born 2017), and son Oscar (born 2019). He is fluent in English and German.
The athlete continues to contribute significantly to equestrian sports while balancing his roles as a business owner, coach, and horse trainer.
Living in Somerby, England, the accomplished athlete, business owner, coach, and horse trainer has a rich history in equestrian sports. He first tried riding at age six in Culcairn, NSW, Australia. By the following year, he was competing on a horse borrowed from his uncle.