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Major League Baseball history is built on moments — swings, pitches, and split-second plays that reshaped seasons and, in some cases, entire franchises. From walk-off home runs in winner-take-all games to clutch hits under October pressure, the biggest plays often came when the stakes were highest. identified the most impactful plays in Chicago Cubs history using data from . Plays were ranked by their Championship Win Probability Added (cWPA), a metric that measures how much a single play changed a team's odds of winning the World Series.

#10. November 02, 2016 (WS Gm 7)
- Score: ahead 2-1 (4th inning, 2 outs)
- Opponent: CLE
- Event: 2B
- Play Description: Double to CF (Fly Ball); B. Zobrist Scores
- cWPA: 10.70%

#9. October 11, 1908 (WS Gm 2)
- Score: tied 0-0 (8th inning, 1 out)
- Opponent: DET
- Event: HR
- Play Description: Home Run (Deep RF); S. Hofman Scores
- cWPA: 11.02%

#8. October 08, 1945 (WS Gm 6)
- Score: tied 7-7 (9th inning, 1 out)
- Opponent: DET
- Event: FC
- Play Description: Fielder's Choice SS; J. Outlaw out at Hm/SS-C-3B; B. Swift to 2B; D. Trout to 1B
- cWPA: 11.34%

#7. October 07, 1935 (WS Gm 6)
- Score: down 2-1 (5th inning, 2 outs)
- Opponent: DET
- Event: HR
- Play Description: Home Run (Deep LF); L. French Scores
- cWPA: 11.67%

#6. October 07, 1935 (WS Gm 6)
- Score: tied 3-3 (9th inning, 0 outs)
- Opponent: DET
- Event: 3B
- Play Description: Triple to CF (Deep CF)
- cWPA: 12.42%

#5. October 08, 1907 (WS Gm 1)
- Score: down 3-2 (9th inning, 2 outs)
- Opponent: DET
- Event: SO
- Play Description: Strikeout E2; H. Steinfeldt Scores (Unearned run)/No RBI; J. Evers to 3B; D. Howard to 1B
- cWPA: 12.56%

#4. October 10, 1908 (WS Gm 1)
- Score: down 6-5 (9th inning, 1 out)
- Opponent: DET
- Event: 1B
- Play Description: Single to CF (Line Drive to LF-CF); F. Schulte Scores; F. Chance Scores; H. Steinfeldt to 3B
- cWPA: 14.54%

#3. November 02, 2016 (WS Gm 7)
- Score: tied 6-6 (9th inning, 1 out)
- Opponent: CLE
- Event: SB
- Play Description: J. Heyward Steals 2B; J. Heyward to 3B (Advanced on throw) on E2 (throw)
- cWPA: 16.65%

#2. October 08, 1945 (WS Gm 6)
- Score: tied 7-7 (12th inning, 2 outs)
- Opponent: DET
- Event: 2B
- Play Description: *WALK-OFF*:Double to LF (Line Drive to Deep SS-3B Hole); B. Schuster Scores
- cWPA: 23.79%

#1. November 02, 2016 (WS Gm 7)
- Score: tied 6-6 (10th inning, 1 out)
- Opponent: CLE
- Event: 2B
- Play Description: Double to LF (Ground Ball); A. Almora Scores; A. Rizzo to 3B
- cWPA: 31.27%