| Postseason: |
Lost World Series (4-2) to New York Yankees Won NL Championship Series (4-1) over Los Angeles Dodgers Won NL Division Series (3-1) over Colorado Rockies |

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Transactions listed are from November 1 of previous year to April 1 of the following year.
October 2, 2008
Released Francisco Rosario.
October 9, 2008
J.D. Durbin granted Free Agency.
October 14, 2008
Travis Blackley granted Free Agency.
Chris Snelling granted Free Agency.
October 31, 2008
Tom Gordon granted Free Agency.
November 3, 2008
Jason Anderson granted Free Agency.
T.J. Bohn granted Free Agency.
Mike Cervenak granted Free Agency.
Matt Childers granted Free Agency.
Jon Knott granted Free Agency.
Stephen Randolph granted Free Agency.
Mike Rouse granted Free Agency.
Rudy Seanez granted Free Agency.
Matt Smith granted Free Agency.
R.J. Swindle granted Free Agency.
Brandon Watson granted Free Agency.
November 4, 2008
Les Walrond selected by the Toronto Blue Jays off waivers.
November 5, 2008
Released So Taguchi.
November 6, 2008
Pat Burrell granted Free Agency.
Jamie Moyer granted Free Agency.
November 13, 2008
Tadahito Iguchi granted Free Agency.
November 18, 2008
Signed Mike Cervenak as a free agent.
Steve Green granted Free Agency.
November 20, 2008
Traded Greg Golson to the Texas Rangers. Received John Mayberry Jr. (minors).
November 28, 2008
Signed Mike Koplove as a free agent.
December 10, 2008
Traded Jsaon Jaramillo (minors) to the Pittsburgh Pirates. Received Ronny Paulino.
December 11, 2008
Drafted Robert Mosebach from the Los Angeles Angels of Anaheim in the 2008 rule 5 draft.
December 12, 2008
Signed Raul Ibanez as a free agent.
Scott Mathieson granted Free Agency.
December 15, 2008
Signed Jamie Moyer as a free agent.
December 16, 2008
Signed Terry Tiffee as a free agent.
December 17, 2008
Signed Wilkin Ruan as a free agent.
December 23, 2008
Signed Gary Majewski as a free agent.
December 25, 2008
Signed Scott Mathieson as a free agent.
December 26, 2008
Signed Justin Lehr as a free agent.
December 29, 2008
Signed Blaine Neal as a free agent.
December 30, 2008
Signed Dave Borkowski as a free agent.
Signed Jason Ellison as a free agent.
January 6, 2009
Signed Chan Ho Park as a free agent.
January 7, 2009
Signed Yorman Bazardo as an amateur free agent.
January 11, 2009
Signed Jason Anderson as a free agent.
Signed Jake Woods as a free agent.
January 16, 2009
Signed Pablo Ozuna as a free agent.
January 22, 2009
Signed Damon Hollins as a free agent.
Signed Jorge Velandia as a free agent.
February 15, 2009
Signed Miguel Cairo as a free agent.
February 27, 2009
Released Adam Eaton.
March 5, 2009
Signed Rodrigo Lopez as a free agent.
March 27, 2009
Traded Ronny Paulino to the San Francisco Giants. Received Jack Taschner.
March 30, 2009
Released Marcus Giles.
April 1, 2009 (Standings)
Released Yorman Bazardo.
Returned Robert Mosebach (earlier draft pick) to the Los Angeles Angels of Anaheim.
May 20, 2009 (Standings)
Selected Steven Register off waivers from the Colorado Rockies.
July 10, 2009 (Standings)
Chris Coste selected by the Houston Astros off waivers.
July 15, 2009 (Standings)
Signed Pedro Martinez as a free agent.
July 29, 2009 (Standings)
Traded Carlos Carrasco (minors), Jason Donald (minors), Jason Knapp (minors), Carlos Carrasco and Lou Marson to the Cleveland Indians. Received Ben Francisco and Cliff Lee.
August 8, 2009 (Standings)
Released Pablo Ozuna.
September 9, 2009 (Standings)
Released Rodrigo Lopez.
2008 Trades and Transactions