Brad Penny.
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The Cubs last victory in the playoffs was in Game 4 of the 2003 NLCS when they defeated the Florida Marlins 8-3. The winning pitcher in that game was Matt Clement.
Aaron Boone hit the game 7, series winning home run in the 2003 ALCS against Boston Red Sox pitcher Tim Wakefield.
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Randy Johnson was the winning pitcher for game 7 of the 2001 World Series.
The Boston Red Sox beat the St. Louis Cardinals in game 4, the final game of the 2004 World Series 3-0. The Winning pitcher was Derek Lowe.