 Simmons akaberekerwa muToronto, Ontario, akatanga kudzidziswa paToronto Newsboys Boxing Club muToronto, Ontario muna 1979. Akanga ari nhengo yeCanada National Boxing Team achienda kunyika dzinopfuura 20 kubva muna 1993 kusvika muna 2000. Muna 1996, Simmons aiva Canadian Olympic chinotsiva muna 91 makirogiramu uremu kupatsanura kuna David Defiagbon 1996 Atlanta, Olympics, Silver medalist. Muna 1995, Simmons akahwina Detroit Golden Gloves muchikamu che91 kg Heavyweight apo maCanada aive achiri kubvumidzwa kukwikwidza kuUS Golden Glove Championships. Aizomiririra Detroit achikwikwidza paNational Golden Gloves muna 1995 muLowell, Mass achikunda makwikwi ake maviri ekutanga, achirasikirwa nemakota-fainari. Pamakwikwi Enyika a1997muBudapest, Hungary, akakunda Macedonia kuburikidza nekutanga kwekutanga, akabva akunda chisarudzo pamapoinzi 18-10 pamusoro peU.S. Davaryll Williamson uye akarasikirwa mumakwikwi ekupedzisira pamapoinzi, 14-10 kuCubas Félix Savón, uyo akaonekwa semumwe wevatambi vepasi rose vakakurumbira. Muna 1997, AIBA yakaronga Mark Simmons semutambi wechishanu akanakisa wetsiva muchikamu chemakumi mapfumbamwe nemapfumbamwe emakirogiramu munyika. Muna 1997, Simmons akahwina menduru yesirivheri kumitambo yeFrancophone muAntananarivo, Madagascar nekurohwa kwekutanga kweMadagascar mumutambo wekutanga, kukunda kwesarudzo yechipiri kukunda France uye kurasikirwa ne14-15 kuCameroon mumutambo wekupedzisira. Pamitambo yeCommonwealth ya1998 muKuala Lumpur, Malaysia, Simmons akahwina menduru yegoridhe muchikamu chemakirogiramu 91 nekukunda Ghana, Wales, neSeychelles. Pa1999 Pan American Games muWinnipeg, Manitoba, Simmons akakunda Jamaica mumakwikwi ekupedzisira, USA mumakwikwi ekupedzisira, uye akarasikirwa naOdlanier Solís weCuba mumakwikwi ekupedzisira ne 4-2 mukutora kumba menduru yesirivheri, kunyangwe achirwa neruoko rwakaputsika. semhedzisiro yeruoko rwake rwakaputsika, Simmons akatadza kutora chikamu mu1999 World Championships yakaitika masvondo maviri mushure mePan Am Games. 