In 2010, Woodland divided his time between the PGA and Nationwide Tours. He continued to struggle for his best form but did not record a single top ten finish on either tour. He did display enough consistency to finish 92nd in the Nationwide Tour money list. Once again, he entered the season-ending qualifying school, and again he finished T-11, to secure a return to full PGA Tour status.
Playing on a Major Medical Extension, returned from a long layoff with a missed cut at the Valero Texas Open, followed by a T32 at the HP Byron Nelson Championship. He last competed in July 2009 at the U.S. Bank Championship in Milwaukee and then underwent surgery to repair a torn labrum in his left shoulder on August 12. Began rehab the next day. Ended the season with three made cuts in eights starts, including his first-career top-25 finish (T21 at the John Deere Classic). Also competed in four Korn Ferry Tour events earlier in the season, missing the cut in all those starts.
In February 2019, Woodland invited Amy Bockerstette, a collegiate golfer with Down syndrome, to play the par-3 16th hole at TPC Scottsdale during a Tuesday practice round at the Waste Management Phoenix Open. After hitting her tee shot into a greenside bunker, Bockerstette surprised Woodland by parring the hole in front of a roaring crowd. The PGA Tour's video capturing the moment went viral, receiving 43 million views across various social media platforms.
At the 2015 Masters Tournament, Rose finished in a tie for second with Phil Mickelson behind winner Jordan Spieth. Rose's 14-under 274 (as well as Mickelson's) was the lowest score by a runner-up in Masters history. He picked up his seventh PGA Tour win at the Zurich Classic of New Orleans in April and added his eighth European Tour win at the UBS Hong Kong Open in October, claiming a narrow 1 stroke triumph after battling Lucas Bjerregaard of Denmark head-to-head over the weekend. .
Dell Technologies Championship: Entered the final round of the Dell Technologies Championship one shot back. Posted four bogeys to make the turn at 1-over before a back-nine 31 to finish runner-up and move to No. 3 in the FedExCup standings. The second-place finish was his ninth top-10 of the season, marking the first time he recorded more than eight top-10s in a season.