In March 2011, Woodland won his first PGA Tour title at the Transitions Championship by one stroke when fellow American Webb Simpson missed a par putt on the final hole. Just a few moments earlier Woodland had scrambled a fantastic par from the same position as Simpson on the last, after hitting his second shot over the back of the green. This win secured Woodland a place at the 2011 Masters Tournament and also elevated him to what was then a career high 53rd in the Official World Golf Ranking. He later earned an invitation into the U.S. Open after moving into the Top 50. He left the tournament with an OWGR ranking of 39th. In November 2011, he won the Omega Mission Hills World Cup with Matt Kuchar. He finished 2011 ranked 17th on the PGA Tour money list and 51st in the OWGR. He had ended 2009 ranked 962 and 2010 591.