[citation needed] 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.

[10] Woodland reached the final of the 2015 WGC-Cadillac Match Play, where he lost to Rory McIlroy, and moved to a career-best 32nd in the OWGR.

[citation needed] In February 2018, Woodland won his third PGA Tour event, at the Waste Management Phoenix Open in a sudden-death playoff over Chez Reavie.

[12] In January 2019, Woodland held the lead entering the final round at the winners-only Sentry Tournament of Champions at Kapalua Resort in Maui, Hawaii.

[13] 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.

1Cancelled due to COVID-19 pandemic QF, R16, R32, R64 = Round in which player lost in match play NT = No tournament "T" = Tied Professional