Five teams that have inflected most pain on the Cleveland Indians since 2016

Record against since 2016: Regular Season (3-5), Postseason (3-4)

Painful Moments

• 2016 World Series: After an improbable playoff run that saw the Cleveland Indians sweep the Boston Red Sox in the ALDS and take down the Toronto Blue Jays in a five-game ALCS, the Indians broke a 62-year American League title drought and sought to end their then 68-year World Series title drought. The team standing in their way was the Chicago Cubs, who sought to end their historic 108-year title drought. Through five games, it appeared it would be the Indians’ title drought coming to an end. Cleveland won game one and after a game, two defeat bounced back to take Games 3 and 4 in Chicago to take a commanding 3-1 series lead. Then the wheels began to fall off. Chicago edged out a 3-2 win in Game 5 after scoring three runs off Trevor Bauer in the bottom of the fourth inning. They then dominated the Indians in Game 6 to set up a decisive Game 7 at Progressive Field. The game was a back and forth affair that made it’s way to extra innings after Cleveland outfielder Rajai Davis hit a dramatic two-run home run off Cubs closer Aroldis Chapman to tie the game at six. After a 17-minute rain delay, extra innings kicked off and the Cubs wasted no time jumping in-front as they plated two runs off Bryan Shaw in the top of the tenth. Cleveland would get a run back in the bottom half of the inning, but it would be too little too late as they dropped a dramatic World Series to the Cubs, breaking the Indians’ heart.
• 2020 season series: Four of the Indians 60 regular season games featured a 2016 World Series with the Chicago Cubs and like that World Series, it did not go well for the Tribe. Chicago swept the four-game set from Cleveland that was split between an August two-game series at Progressive Field and a September two-game set at Wrigley Field. In Chicago, the Cubs walked-off the Indians on back-to-back nights while the Tribe were in the midst of a season-long eight-game losing streak.
• David Ross, the Indians killer: In both the 2016 World Series and 2020 regular season sweep, David Ross played a major role on inflicting pain upon the Cleveland Indians. In Game 7 of the 2016 World Series, Ross delivered a clutch solo-run home run in the top of the sixth inning off ALCS MVP Andrew Miller to 6-3 in a game Cleveland ended up losing by one run. Four years later, Ross again burned the Indians. In his first-year as Cubs manager Ross guided his Cubs to a four-game sweep of the Indians, which would be crucial to Chicago clinching the NL Central title as they ended up winning the division by three games over the Cardinals and Brewers.