On June 23, 2009, Jennings received a new three-year extension which paid him $26.35 million and included $16 million guaranteed. It also included a $11.25 million signing bonus. Jennings caught a game-winning pass on September 13, 2009, on a 3rd and two play, where the Packers ran a play action fake and rolled Aaron Rodgers out to the left, who then threw a 50-yard pass to Jennings to defeat the Chicago Bears in the season opener. In the Packers 2009 Wild Card game against the Arizona Cardinals, Jennings had 8 receptions for 130 yards, scoring 1 touchdown.