3.) Monday, September 2: Pittsburgh Pirates 5 - Chicago Cubs 3
This could be considered the game that extinguished any remaining hope the Cubs had to get into the postseason. After returning home from the insane 8-1 road trip in which the offense scored 89 runs, Chicago was within 3 1/2 of the final wild-card spot in the NL. Wrigley Field was buzzing as the team still had some life. It all seemed good when the Cubs had a 3-0 lead by the top of the eighth, needing just six more outs to secure another victory.
Jorge Lopez, who had been very good since coming to Chicago but was a bit banged up, got the eighth inning. He surrendered back-to-back singles before giving up a game-tying three-run homer to Bryan Reynolds. In the blink of an eye, the lead was gone. After finally getting an out, longtime Cubs killer Andrew McCutchen gave the North Siders another groin kick with a go-ahead solo shot to left. The lead was gone, but the Cubs offense was hot and the Pirates bullpen was horrific. Cody Bellinger and Patrick Wisdom came close to bringing Wrigley back to life with some deep fly balls, but neither quite got over the fence. The Pirates added a run in the top of the ninth and the Cubs went down quietly in the bottom of the inning to close it out.
No matter how a Cubs fan felt about their postseason chances, this game was a massive blow to any sort of hope. There are arguably worse blown games than this one, but the weight it carried got it on the list.