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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 Pittsburgh Pirates 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. October 17, 1971 (WS Gm 7)
- Score: tied 0-0 (4th inning, 2 outs)
- Opponent: BAL
- Event: HR
- Play Description: Home Run (Deep LF-CF)
- cWPA: 14.84%

#9. October 14, 1909 (WS Gm 6)
- Score: down 5-3 (9th inning, 0 outs)
- Opponent: DET
- Event: Out
- Play Description: Reached on E3 (catch)/Sacrifice Bunt (Bunt to C); D. Miller Scores (Unearned run)/No RBI; B. Abstein to 3B; O. Wilson to 1B
- cWPA: 15.90%

#8. October 15, 1925 (WS Gm 7)
- Score: down 6-4 (7th inning, 0 outs)
- Opponent: WSH
- Event: 2B
- Play Description: Double to LF (Fly Ball); E. Moore Scores (Unearned run)
- cWPA: 16.59%

#7. October 13, 1960 (WS Gm 7)
- Score: tied 0-0 (1st inning, 2 outs)
- Opponent: NYY
- Event: HR
- Play Description: Home Run (Line Drive to Deep RF); B. Skinner Scores
- cWPA: 19.22%

#6. October 17, 1979 (WS Gm 7)
- Score: down 2-1 (8th inning, 2 outs)
- Opponent: BAL
- Event: Out
- Play Description: Flyball: RF (Deep RF)
- cWPA: 19.82%

#5. October 17, 1979 (WS Gm 7)
- Score: down 1-0 (6th inning, 1 out)
- Opponent: BAL
- Event: HR
- Play Description: Home Run (Deep RF); B. Robinson Scores
- cWPA: 29.25%

#4. October 15, 1925 (WS Gm 7)
- Score: tied 7-7 (8th inning, 2 outs)
- Opponent: WSH
- Event: 2B
- Play Description: Ground-rule Double (Fly Ball to Deep RF Line); C. Bigbee Scores (Unearned run); E. Moore Scores (Unearned run); M. Carey to 3B
- cWPA: 29.26%

#3. October 15, 1925 (WS Gm 7)
- Score: down 7-6 (8th inning, 2 outs)
- Opponent: WSH
- Event: 2B
- Play Description: Double to LF (Fly Ball); E. Yde Scores
- cWPA: 29.49%

#2. October 13, 1960 (WS Gm 7)
- Score: tied 9-9 (9th inning, 0 outs)
- Opponent: NYY
- Event: HR
- Play Description: *WALK-OFF*:Home Run (Fly Ball to Deep LF)
- cWPA: 36.74%

#1. October 13, 1960 (WS Gm 7)
- Score: down 7-6 (8th inning, 2 outs)
- Opponent: NYY
- Event: HR
- Play Description: Home Run (Fly Ball to Deep LF); D. Groat Scores; R. Clemente Scores
- cWPA: 63.62%