Biggest plays in Chicago Cubs history

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. Stacker identified the most impactful plays in Chicago Cubs history using data from Stathead. 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%