After a 2009 season in which he blew only two saves, Street struggled during the playoffs for the Rockies. In Game 4 of the 2009 National League Division Series, Street entered the ninth inning with the Rockies leading 4–2. He was able to record the first two outs before allowing three runs that gave the Phillies a 5–4 win and a series victory. Before the 2010 season, Street and the Rockies agreed on a three-year $22.5 million contract with an option for 2013.