In August 2020, Wolff finished in a tie for fourth place at the PGA Championship, his first major championship appearance, after a final-round 65 (five-under par). Six weeks later, in September, he led the U.S. Open at Winged Foot by two strokes heading into the final day after returning a third-round score of 65 (five-under par), the joint lowest round of the tournament. A final round of 75 (five-over par) saw him finish as runner-up, six strokes behind winner Bryson DeChambeau. His second top-five finish from his first two major championships earned him $1,350,000.