After turning professional, Woodland played in a handful of tournaments on the Nationwide Tour in 2007 and 2008. At the end of the 2008 season, he entered the
Qualifying school for the
PGA Tour, and finished in a tie for 11th, which was good enough to earn him a full card to play on the PGA Tour in 2009. However, he struggled for form in his debut season, making just eight cuts in 18 appearances before a shoulder injury cut his golfing year short in July. 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. Woodland's second tournament of 2011 was the
Bob Hope Classic, where he and
Jhonattan Vegas finished tied for first place at 27-under-par; Vegas edged out Woodland in a playoff for the title. This was his first top-10 finish on either of the two main tours. 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. 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. In February
2018, Woodland won his third PGA Tour event, at the
Waste Management Phoenix Open in a hole-by-hole playoff over
Chez Reavie. After finishing tied at 18 under, Woodland won with a par on the first extra hole to end a five-year drought on tour. Woodland moved up to fifth in the season's FedEx Cup standings. Woodland held the 36-hole lead at the
PGA Championship in
2018 with a total 130, which was a tournament record through the first two rounds. He led by a stroke over
Kevin Kisner at the halfway stage. He started the final round at nine under par, three shots behind leader
Brooks Koepka. He finished in a tie for sixth with a score of 10 under par, six strokes behind the winner Koepka. 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. He shot a five-under-par 68 but still lost to champion
Xander Schauffele who shot a course record-tying 62. 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
U.S. Open in June
2019, Woodland held the 54-hole lead at
Pebble Beach Golf Links. On Sunday, he shot a 2-under-par 69 for 271 (−13), which gave him a three-shot margin over the runner-up, two-time defending champion Koepka. Woodland became the fourth champion in U.S. Open history who was double-digits under-par. The victory was his first major and his sixth professional win. In his previous thirty starts in majors, Woodland had only carded two top-ten finishes, both in the PGA Championship (2018,
2019). The win at the U.S. Open moved him from 25th to 12th in the Official World Golf Ranking. At the post-win press conference, Woodland
FaceTimed Bockerstette live, telling her "I used your positive energy." Two days later, Woodland joined Bockerstette with a surprise appearance on
The Today Show where, pointing to the U.S. Open trophy in Bockerstette's hands, he told her "We won this together." In December 2019, Woodland played on the U.S. team at the
2019 Presidents Cup at
Royal Melbourne Golf Club in Australia. The U.S. team won 16–14. Woodland went 1–2–1 and lost his Sunday singles match against
Im Sung-jae. Woodland finished runner-up at the
Houston Open in March 2025, one stroke behind
Min Woo Lee. This was Woodland's first top-5 finish since his brain surgery in 2023. In March 2026, Woodland shot a tournament-record, 21-under 259 at the
Houston Open to win the event by five strokes over
Nicolai Højgaard. It was Woodland's first professional victory since the 2019 U.S. Open and his fifth PGA Tour victory. The win earned him a spot in the field for the
Masters Tournament. ==Personal life==