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 91 kg. 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, and losing a 5 round 14-10 decision to Cuba's three time Olympic Gold medalist, Félix Savón, who was highly regarded as one of the world's greatest boxers, giving him an AIBA ranking of 5th in the world. In 1997, Simmons would win 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 Solis of Cuba in the final by a 4-2 score in the taking home the silver medal, despite boxing with a broken hand.
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