Sentry Tournament of Champions: Lost to Justin Thomas in a three-hole playoff at the Sentry Tournament of Champions, falling to 2-2 for his career in playoffs. Marked his sixth career runner-up on TOUR and first since the 2018 Valspar Championship. Became the first player since the tournament moved to The Plantation Course at Kapalua in 1999 with 100 putts or fewer in a single year (99). One-Putt Percentage of 62.50 percent was the best on TOUR since Bud Cauley at the 2018 RBC Heritage (65.28%).

Advanced to the FedExCup Playoffs for the fourth consecutive season, making it to the TOUR Championship for the third consecutive time. Entered the Playoffs finale in the No. 2 position in the FedExCup standings and finished T24 at East Lake to end his season a career-best No. 3 in the FedExCup standings. Recorded 18 top-25 finishes from 28 starts. Of those, 11 were top-10 showings, including his first FedExCup Playoffs victory at The Barclays. Eleven top-10s was second only to Dustin Johnson who led the TOUR with 15.

DP World Tour Championship Dubai: Carded a final-round 67 to win the European Tour's DP World Tour Championship in Dubai, where a late slip from Justin Rose handed Tommy Fleetwood the Race to Dubai title. Came home in 33 to get to 19-under and win his second Rolex Series title by one shot over Shane Lowry and Kiradech Aphibarnrat. Awarded the European Tour's Sir Henry Cotton Rookie of the Year award earlier in the week, added this win to his Dubai Duty Free Irish Open Hosted by the Rory Foundation title to become the first player to win multiple Rolex Series events.

Season highlighted by three wins and a seventh-place finish in his FedExCup title defense. Made the cut in 21 of 23 starts, earning double-digit top-10s (10) for the second consecutive season and reaching 20 top-25s for the first time in his career. Became the first player since Tiger Woods in 2006 and 2007 to lead the TOUR in earnings in consecutive seasons. Accumulated a score of 155-under-par for the season, second-best on TOUR (Dustin Johnson, 189-under). Earned inaugural appearance on the United States Ryder Cup team.

Sentry Tournament of Champions: Defeated Patrick Reed and Xander Schauffele in a playoff to win the Sentry Tournament of Champions for the second time, earning his 12th PGA TOUR title at age 26 years, 251 days. Became the third player since 1960 to win 12 times before turning 27, joining Jack Nicklaus and Tiger Woods. Represented his third win in a six-start stretch on TOUR. Joined Stuart Appleby (3), Geoff Ogilvy (2) and Dustin Johnson (2) as players to win the event multiple times since it moved to The Plantation Course at Kapalua in 1999. Led the field in Birdies (24) and Par-3 Scoring Average (2.75). Improved to 3-1 in his career in playoffs.

Nationwide Children's Hospital Championship: After finishes of second, third, T4, T5 (twice) and T6, finally broke through with a win at the Nationwide Children's Hospital Championship on the Tour's toughest course of the year. His winning score was 6-under 278, with the field's average score 1.59-over par. Trailed South Africa's Richard Sterne by three shots with four holes to play only to find himself in a playoff after Sterne bogeyed Nos. 15, 16 and 17. A wedge from 75 yards to three feet on the 18th hole at Ohio State University GC's Scarlet Course sealed the victory with both his parents and grandparents in his Sunday gallery. Became the fourth-youngest winner in Tour history, trailing only Jason Day, Patrick Cantlay and Danny Lee. 

THE NORTHERN TRUST: Entering the final round with a one-shot lead over Abraham Ancer, carded a 2-under 69 to edge Ancer by one stroke and win THE NORTHERN TRUST for the second time in his career. The win, his seventh on the PGA TOUR, moved him to No. 2 in the FedExCup standings and guaranteed him a spot in the season-ending TOUR Championship. Converted the 54-hole lead/co-lead into a win for the fifth time in seven attempts on TOUR. Became the seventh player to win multiple titles at the event and second to do so in the FedExCup era, joining Dustin Johnson.
On April 14, Schauffele tied for second in the Masters Tournament, one stroke behind champion Tiger Woods. After opening with a 1-over 73, recorded rounds of 65-70-68 to finish T2 at the Masters Tournament with Dustin Johnson and Brooks Koepka. Schauffele's finish at the Masters Tournament represented his third top-five in eight starts at major championships (T5 at 2017 U.S. Open, T2 at 2018 Open Championship, T2 at 2019 Masters Tournament). He led the field with 25 birdies, becoming the third player since 1980 to have 25 or more birdies in a single Masters, joining Phil Mickelson (25 in 2001) and Jordan Spieth (28 in 2015).[25]