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What if the Cubs had won one more game in September 2018?

This is such recent history that you no doubt remember the sequence well.

The Cubs had nine postponed games in 2018, resulting in a schedule crunch in August and September. The team’s last scheduled off day was August 20, and after that they played 41 games (including the tiebreaker against the Brewers and the wild-card game against the Rockies) in 43 days, the only “off” days coming with two rainouts in Washington. That resulted in the team having to fly from Chicago to Washington to Chicago within a 36-hour period — and there play an extra-inning game in which Pedro Strop was injured running the bases.