Born in Toronto, Ontario, Simmons first began training at the Toronto Newsboys Boxing Club in Toronto, Ontario in 1979. He was a member of the Canadian National Boxing Team from 1993 to 2000. In 1996, Simmons was the Canadian Olympic alternate in the 91 kg weight division to David Defiagbon. In 1995, Simmons won the Detroit Golden Gloves in the 91 kg Heavyweight division when Canadians were still allowed to compete at the US Golden Glove Championships. He would then represent Detroit competing at the 1995 National Golden Gloves in Lowell, Mass winning his first two bouts, losing in the quarter-finals. His first major international tournament was the 1997 World Championships in Budapest, Hungary, where he defeated Macedonia via a first round knock out, then winning a decision over USA's Davaryll Williamson and losing a 5-round 14-10 decision to Cuba's three-time Olympic gold medalistFélix Savón, who was highly regarded as one of the world's greatest amateur boxers, giving him an AIBA ranking of fifth in the world. In 1997, Simmons won a silver medal at the Francophone games in Antananarivo, Madagascar with a first round knock out over Madagascar in the first fight, a second-round decision victory over France and a 14-15 loss to Cameroon in the final. At the 1998 Commonwealth Games in Kuala Lumpur, Malaysia, Simmons won the gold medal in the 91 kg heavyweight division with victories over Ghana, Wales, and the Seychelles. At the 1999 Pan American Games in Winnipeg, Manitoba, Simmons defeated Jamaica in the quarter-finals, USA in the semi-final, and lost to Odlanier Solís of Cuba in the final by a 4-2 score in the taking home the silver medal, despite boxing with a broken hand. Simmons had qualified a place under the 91 kg heavyweight division at the 2000 Olympic Qualification tournament in Tijuana, Mexico with victories over Venezuela, Jamaica, Puerto Rico. At the 2000 Summer Olympics Simmons defeated Iran's Rouhollah Hosseiniin the round of 16 by a score of 11–6, suffering a broken hand in this bout. Simmons then lost the guaranteed bronze medal match to Germany's Sebastian Köber in the quarterfinal by a score of 16–1.
Personal life
Simmons graduated with a Bachelor of Science degree from York University in 2000. Simmons did not turn professional in spite of offers, and retired from boxing, going into work as a pharmaceutical sales representative. He has appeared in movies including Cinderella Man, working along his fellow Canadian teammate and roommate Troy Amos-Ross, playing heavyweight boxer Art Lasky. In 2011, Simmons joined the Ontario Athletic Commission as a professional boxing referee.
