Masters Tournament: Finished runner-up at the Masters, one stroke behind Patrick Reed, for his best result at the event. For the first time in eight starts at Augusta National, recorded four par-or-better rounds (70-72-65-67). Earned his third runner-up in a major (2nd/2018 Masters Tournament, T2/2014 The Open Championship, T2/2014 U.S. Open) and third top-five in the last four (2nd/2018 Masters Tournament, T5/2017 Open Championship, T5/2017 U.S. Open). With third-round 65, was one of just four players to post a bogey-free round during the week (Rory McIlroy/65, Jon Rahm/65, Si Woo Kim/65) with all four occurring in the final round.
On August 26, 2018, he won The Northern Trust for his first playoff victory; in the process, he established a new record for the tournament when held at the Ridgewood Country Club, with a score of 266, besting the old Ridgewood record of 270, which was set in 2014 by Hunter Mahan. The following week, he won at the Dell Technologies Championship played at TPC Boston in Norton, Massachusetts, with a final score of −16, two shots clear of Justin Rose. This put him over 2000 points ahead of the second place player, Dustin Johnson, in the FedEx Cup rankings. This margin secured him top seeding at The Tour Championship, regardless of his finish at the BMW Championship. This also marked his fourth win on tour, third for the year, and second during the playoffs. At the Tour Championship, DeChambeau finished 19th out of 30 participants. As a result, he fell to 3rd in the FedEx Cup, winning $2,000,000.
PGA Championship: Finished T3 and two strokes behind McIlroy at the PGA Championship in his 20th major championship start, with T19 in 2013 the previous-best finish in four prior PGA Championship starts. Became the first to claim top-five finishes in all four majors since Woods in 2005. Since 1934, is just the third player to perform the feat, joining Woods in 2000 and 2005 and Jack Nicklaus in 1971 and 1973. Played all four majors in 32-under, with McIlroy second on the list, at 27-under.
After a tie for fifth at the Masters in April, Fowler had his best finish of 2014 at the U.S. Open at Pinehurst No. 2 in North Carolina. Fowler was runner-up with Erik Compton at −1, best finishes for both at a major, but they were eight strokes behind champion Martin Kaymer. Fowler had another second-place finish, at the Open Championship at Royal Liverpool Golf Club in Hoylake, England. He began the final round six strokes behind Rory McIlroy and finished the day tied for second with Sergio García at −15, two strokes behind McIlroy. At the next major in August, the PGA Championship, Fowler, Phil Mickelson, Henrik Stenson, and McIlroy battled for the title on a rain-soaked Valhalla Golf Club, near Louisville. Despite holding the lead for a good portion of the day, Fowler tied for third. He was only the third player, along with Jack Nicklaus and Tiger Woods, to have finished in the top 5 in all four majors in one calendar year, but the first not to win (Jordan Spieth became the fourth player in 2015). Fowler had 10 top-10 finishes during the 2013–14 season. His 8th-place finish at The Tour Championship moved him to 10th in the world golf rankings.
Shell Houston Open: After opening with an 8-under 64 for a one-stroke lead on day one, added rounds of 71-67-70 to finish T3 at the Shell Houston Open. Erased a seven-shot deficit in the third round and started the final round three shots behind 54-hole leader Sung Kang, but a final-round 70 saw him finish four strokes behind winner Russell Henley. With 27 birdies on the week (tied for most with Henley), marked his most birdies in a single event.