Stricker won his fifth PGA Tour title at Colonial in Texas at the end of May 2009, with a playoff win over Tim Clark and Steve Marino. The win was aided by a chip-in on the 71st hole. He won again in July at the John Deere Classic in Silvis, Illinois. After the second round was rained-out on Friday, the field was forced to play 36 holes on Sunday. Stricker shot an afternoon round of 64, which included a hole-out wedge shot for eagle on the 6th hole, and by three strokes over runners-up Zach Johnson, Brandt Snedeker, and Brett Quigley. He also matched his career low round on tour with a second round of 61 (−10).