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Chicago Cubs Award Winners

The Cubs have existed for over a century. Can you guess every single player to take home one of MLB's most prestigious awards?
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BigDaddyPeach23
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Last updated: November 11, 2025
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First submittedDecember 5, 2024
Times taken32
Average score48.2%
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Manager of the Year
1984
Jim Frey
1989
Don Zimmer
2008
Lou Piniella
2015
Joe Maddon
Home Run Derby Champion
1987
Andre Dawson
1990
Ryne Sandberg
2000
Sammy Sosa
Silver Slugger
1982
Leon Durham
1984
Ryne Sandberg
1987
Ryne Sandberg
1987
Andre Dawson
1988
Ryne Sandberg
1989
Ryne Sandberg
1990
Ryne Sandberg
1991
Ryne Sandberg
1992
Ryne Sandberg
1995
Sammy Sosa
1998
Sammy Sosa
1999
Sammy Sosa
2000
Sammy Sosa
2001
Sammy Sosa
2002
Sammy Sosa
2005
Derrek Lee
2005
Michael Barrett
2006
Carlos Zambrano
2008
Carlos Zambrano
2009
Carlos Zambrano
2011
Aramis Ramirez
2016
Anthony Rizzo
2016
Jake Arrieta
2018
Javier Baez
2023
Cody Bellinger
2025
Kyle Tucker
MVP
1911
Frank Schulte
1929
Rogers Hornsby
1930
Hack Wilson
1935
Gabby Hartnett
1945
Phil Cavaretta
1952
Hank Sauer
1958
Ernie Banks
1959
Ernie Banks
1984
Ryne Sandberg
1987
Andre Dawson
1998
Sammy Sosa
2016
Kris Bryant
World Series MVP
2016
Ben Zobrist
NLCS MVP
2016
Jon Lester
2016
Javier Baez
All Star Game MVP
1975
Bill Madlock
Cy Young Award
1971
Fergie Jenkins
1979
Bruce Sutter
1984
Rick Sutcliffe
1992
Greg Maddux
2015
Jake Arrieta
Rookie of the Year
1961
Billy Williams
1962
Ken Hubbs
1989
Jerome Walton
1998
Kerry Wood
2008
Geovany Soto
2015
Kris Bryant
Gold Glove
1960
Ernie Banks
1962
Ken Hubbs
1964
Bobby Shantz
1964
Ron Santo
1965
Ron Santo
1966
Ron Santo
1967
Ron Santo
1967
Randy Hundley
1968
Ron Santo
1968
Glenn Beckert
1969
Don Kessinger
1970
Don Kessinger
1983
Ryne Sandberg
1984
Ryne Sandberg
1984
Bob Dernier
1985
Ryne Sandberg
1986
Ryne Sandberg
1986
Jody Davis
1987
Ryne Sandberg
1987
Andre Dawson
1988
Ryne Sandberg
1988
Andre Dawson
1989
Ryne Sandberg
1990
Ryne Sandberg
1990
Greg Maddux
1991
Ryne Sandberg
1991
Greg Maddux
1992
Greg Maddux
1992
Mark Grace
1993
Mark Grace
1995
Mark Grace
1996
Mark Grace
2004
Greg Maddux
2005
Greg Maddux
2005
Derrek Lee
2007
Derrek Lee
2012
Darwin Barney
2016
Anthony Rizzo
2016
Jason Heyward
2017
Jason Heyward
2018
Anthony Rizzo
2019
Anthony Rizzo
2020
Anthony Rizzo
2020
Javier Baez
2022
Ian Happ
2023
Ian Happ
2023
Dansby Swanson
2023
Nico Hoerner
2024
Ian Happ
2025
Ian Happ
2025
Nico Hoerner
2025
Pete Crow-Armstrong
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