On June 3, 2018, DeChambeau won the Memorial Tournament in Dublin, Ohio, in a sudden-death playoff against Kyle Stanley and An Byeong-hun, after the three finished regulation play tied at −15. After Stanley bogeyed the first hole of sudden death, DeChambeau then proceeded to win with a birdie on the second hole, giving him his second win on the tour.
The Honda Classic: After beginning the final round of The Honda Classic with a four-stroke lead, posted a 1-over 71 to win by the same margin for his fourth career PGA TOUR title. It marked the first of five 54-hole leads he converted to victory. Opened with back-to-back 66s for the second consecutive year and posted a 65 in the third round to post the best 54-hole total since the event moved to PGA National in 2007 at 13-under 197. Seized the 54-hole lead with the widest margin of his career entering a final round. Turned in 2-over 37, but posted three birdies on the back nine to take command of the tournament. Despite bogeys on the 71st and 72nd holes, claimed his first victory since the 2015 Dell Technologies Championship. Finished the week second in Strokes Gained: Putting (7.392) and moved to 10th in the FedExCup standings and ninth in the Official World Golf Ranking, his first time in the top 10 since the 2016 BMW Championship.
Fowler is one of four golfers in the "Golf Boys" group along with fellow PGA Tour players Ben Crane, Bubba Watson and Hunter Mahan. The Golf Boys released a YouTube video of the song "Oh Oh Oh" on the eve of the 2011 U.S. Open. Farmers Insurance is donating $1,000 for every 100,000 views of the video. The charitable proceeds will support both Farmers and Ben Crane charitable initiatives.
After finishing fifth in the Hyundai Tournament of Champions in Hawaii, Fowler claimed his first victory of 2016 in the Abu Dhabi HSBC Golf Championship on the European Tour. He shot a final round of 69 to finish one clear of Belgium's Thomas Pieters. Two weeks later, Fowler was in contention to win again but lost out to Japan's Hideki Matsuyama in a playoff at the Waste Management Phoenix Open. On March 7, Fowler sparked fantastic scenes after sinking a hole-in-one with fellow tour pro Luke Donald's pitching wedge to win $1 million for Ernie Els' charity, Els for Autism.
On July 16, 2017, DeChambeau earned his first PGA Tour victory by winning the John Deere Classic by a single stroke over Patrick Rodgers. He carded a round of 65 in the final round to win his maiden title in his 40th start on tour. The win coming the week before, gained DeChambeau a place in the 2017 Open Championship, where he missed the cut after rounds of 76–77 (+13).