Kammala jumla mai zuwa: Montgomery ya yi rawar gani a kakar wasa ta 2016, yana taka muhimmiyar rawa a gasar zakarun na kungiyar. Gabaɗaya ya tafi 1-1, gami da bayyanar 11, innings da aka jefa, da ERA na 3.14. Musamman, Montgomery ya sauƙaƙe Carl Edwards Jr. a ƙarshen 10th inning a Game 7 na
Gasar cin kofin duniya. Tare da mai gudu a kan na farko da kuma biyu a cikin wasa guda daya, ya gama wasan tare da ƙasa zuwa na uku. Montgomery ya sami nasarar farko a cikin aikinsa, ya lashe gasar cin kofin duniya don Chicago Cubs a karon farko a cikin shekaru 108.