The Kansas native finally broke through and won his first major championship at the 2019 U.S. Open at Pebble Beach (Calif.) Golf Links. In the final round, he held off hard-charging Brooks Koepka by three strokes. Koepka was seeking a third consecutive title. Woodland's previous victory had come in the 2018 WM Phoenx Open in a playoff over 2001 U.S. Amateur Public Links champion Chez Reavie. He also claimed the 2013 Reno-Tahoe and 2011 Transitions Championship. Attended Division II Washburn University in Kansas on a basketball scholarship, but left after his freshman season to play golf at the University of Kansas. He won four collegiate tournaments for KU before turning professional in 2007. In 2015, he reached the final of the WGC-Cadillac Match Play before losing to Rory McIlroy. Played on the victorious 2019 U.S. Presidents Cup Team in Australia.
U.S. Open Record
| Year | Site | Scores | To Par | Finish |
| 2021 | Torrey Pines Golf Course (South Course) | 74-71-73-74--292 | +8 | T-50 |
| 2020 | Winged Foot Golf Club (West Course) | 74-74 | +8 | MC |
| 2019 | Pebble Beach Golf Links | 68-65-69-69--271 | -13 | Win |
| 2018 | Shinnecock Hills Golf Club | 79-69-70-75--293 | +13 | T-36 |
| 2017 | Erin Hills | 72-73-73-74--292 | +4 | T-50 |
| 2015 | Chambers Bay | 74-77 | +11 | MC |
| 2014 | Pinehurst Resort & C.C. (Course No. 2) | 72-71-75-74--292 | +12 | T-52 |
| 2012 | The Olympic Club (Lake Course) | 74-77 | +11 | MC |
| 2011 | Congressional Country Club (Blue Course) | 73-71-73-68--285 | +1 | T-23 |
| 2010 | Pebble Beach Golf Links | 76-76 | +10 | MC |
| 2009 | Bethpage State Park (Black Course) | 73-66-76-77--292 | +12 | T-47 |