A ranar 25 ga Oktoba, 2016, Heyward, tare da abokan wasan Dexter Fowler, Addison Russell, da Carl Edwards Jr., sun zama 'yan Afirka na farko da za su buga wa Cubs wasa a
Wasan gasar cin kofin duniya. An yaba wa Heyward da jagorantar taron 'yan wasa masu ban sha'awa a lokacin jinkirin ruwan sama na mintina 17 a kusa da ƙarshen Wasan 7 na Wasannin Duniya na 2016. A ƙarshe Cubs sun ci wasan 8<unk>7 bayan wasan kwaikwayo 10, kuma ya ba su gasar zakarun duniya ta farko a cikin shekaru 108. A ranar 9 ga Nuwamba, Heyward ya zama dan wasa na farko a tarihin Major League Baseball don lashe lambar yabo ta Golden Glove sau uku a jere tare da kungiyoyi uku daban-daban (Braves, Cardinals, da Cubs).