On Wednesday, February 26, 2025, received the PGA TOUR Courage Award. The initial announcement was made during an exclusive interview with Michael Strahan on ABC's "Good Morning America", followed by a formal presentation at the Cognizant Classic in The Palm Beaches.

As the recipient of the PGA TOUR Courage Award in 2025, received $25,000 charitable contribution from the PGA TOUR for a charity of his choosing. Woodland designated Champion Charities, an organization dedicated to research and patient support for brain tumors, brain diseases, and brain traumas. Woodland and his wife, Gabby, matched the donation with $25,000 of their own for Champion Charities.

Featured in Season 3, Episode 6 of Netflix's Full Swing, an immersive documentary series which follows life on the PGA TOUR. Woodland's recovery from surgery to remove a brain lesion in September 2023, and his subsequent return to professional golf, are documented in the episode of Full Swing.

In September 2023, two days after Woodland underwent brain surgery, his alma mater - the University of Kansas - announced it was naming its golf practice complex after him. Used by the Jayhawk men's and women's teams, the Kansas Board of Regents approved naming the facilities the Gary Woodland Golf Complex -- which includes practice holes, a driving range and putting facilities -- at the privately-owned Jayhawk Club in Lawrence, Kansas.

Inducted into the Kansas Golf Hall of Fame on October 7, 2024. He was part of the same inductee class that included four-time PGA TOUR winner Woody Austin and PGA TOUR winner Matt Gogel. Another notable member of the Kansas Golf Hall of Fame is Tom Watson, who was inducted in 1991.

Inducted into the Topeka Sports Hall of Fame in June 2017, recognizing his history in the community as an All-State basketball player and professional golfer.

Prior to his college golf career at University of Kansas, played one season (2002-03) of basketball at Washburn University, an NCAA Division II program in Topeka, Kansas. The Ichabods went 26-6 and earned an NCAA Tournament berth in Woodland's lone season, which saw him play in all 32 games (four starts) as a point guard. Woodland averaged 17.4 minutes and 6.0 points a game, in addition to shooting 31.7 percent from 3-point range.

Named All-State in basketball and helped Shawnee Heights High School win Class 5A state basketball titles in 2000 and 2002.

Favorite college team is the Kansas Jayhawks and favorite professional team is the Kansas City Chiefs.

Marks his ball with a 1984 half-dollar coin given to him by his mother. The year 1984 signifies the year he was born.

Played four seasons at University of Kansas (2003-07), the school he always dreamed of attending, and graduated with a Sociology degree in 2007. Earned four collegiate victories while at Kansas, including three wins as a senior (2006-07 season) and finished with a 73.33 career scoring average. Also earned All-Big 12 Conference selections in 2006 and 2007.

Won the 2005 and 2007 Kansas Amateur Championships.