Nyorai kuenderera mberi kweiyi ndima - Montgomery aive nehunyanzvi hwekuita postseason muna 2016, achitamba chinzvimbo chakakosha mukumhanya kwechikwata. Pamwe chete akaenda 1-1, kusanganisira 11 kuoneka, innings pitched, uye 3.14 ERA. Zvikurukuru, Montgomery akabvisa Carl Edwards Jr. pasi pe 10th inning mu Game 7 yeWorld Series
. Nemumhanyi ari pabhesi rokutanga uye maviri akabuda mumutambo weimwe-run, akapedza mutambo nechikamu chepasi kusvika pabhesi rechitatu. Montgomery akawana ruponeso rwake rwokutanga rwebasa, achikunda World Series nokuda kweChicago Cubs kwenguva yokutanga mumakore 108.