[22] When pitchers and catchers reported on February 13, three of twelve pitching positions were set: starter Paul Maholm, set-up man John Grabow, and closer Matt Capps.
[21] Beginning March 5, Ian Snell, Ramón Vázquez, and John Grabow represented their countries in the 2009 World Baseball Classic.
[33] In the team's home opener on April 13, Zach Duke pitched a complete game shutout, as the Pirates defeated the Houston Astros, 7–0.
[34] In the game, both the Pirates and the Astros wore Pittsburgh Police hats in honor of three officers who were shot and killed on April 4.
[35] The pre-game ceremonies honored the officers, as well as former Pirates pitcher and current broadcaster Steve Blass for this 50th season with the team, and included a flyover by four Apache helicopters from the 1/104th Attack Reconnaissance Battalion of the Pennsylvania Army National Guard.
[36] In the first Saturday afternoon game in Pittsburgh since 2005, Craig Monroe hit two three-run home runs in consecutive innings to give the Pirates their first back-to-back victories of the season.
[37] On April 21, catcher Ryan Doumit announced that surgery was needed to fix a broken bone in his wrist, and that he would miss eight to ten weeks.
[43] The team was tied for third place in the NL Central division, four games behind the St. Louis Cardinals, who finished the month with the league's best record.
[47] The Pirates were swept during a two-game series in St. Louis—the losses extended Pittsburgh's losing streak to five consecutive road games and nine out of their past ten overall.
[50] On May 13, Adam LaRoche became the first player in MLB history to have a home run taken away due to instant replay, during a procedure put into effect in August 2008.
On June 4, the Pirates traded All Star Nate McLouth to the Atlanta Braves for three minor league players, including future starting pitcher Charlie Morton.
In the game against the Royals on June 26, starting pitcher Virgil Vasquez earned his first win in his major league debut.
On June 30, starting center fielder Nyjer Morgan and relief pitcher Sean Burnett were traded to the Washington Nationals in exchange for Lastings Milledge and Joel Hanrahan.
Hanrahan was put on the starting roster immediately, but Milledge was forced to go through a series of rehab-starts in AAA Indianapolis before being called up, due to an existing injury.
On July 17, in the first of a three-game series against the San Francisco Giants, reliever Evan Meek picked up his first win of the season in a 14-inning game.
On July 20, in the first of a three-game series against the Brewers, the benches were cleared in the eighth inning when Milwaukee pitcher Chris Smith hit Pittsburgh reliever Jeff Karstens with a pitch.
After the game, the Pirates traded three-time All-Star second baseman Freddy Sanchez to the Giants for minor league pitcher Tim Alderson.
This started an eight-game losing streak, against the Nationals, the Diamondbacks, and the Cardinals, which ended August 11 when the Pirates defeated the Rockies in Colorado.
The Pirates didn't win a game the rest of the month, being swept by the Brewers and the Reds in a series stretching into September.
They then lost the first game of a three-game series against the Cubs, giving them their 82nd loss, and setting the record for most consecutive losing seasons in any sport since the 1933–1948 Philadelphia Phillies.