After beginning the day two shots off pace, he fired a 4-under 68 that included a birdie putt at the par-4 17th to move into a tie at 11-under and force the fourth playoff in Insperity Invitational tournament history. The 51-year-old birdied the first playoff hole on No. 18 to win the 2025 Insperity Invitational over 36-hole co-leader and World Golf Hall of Fame member Retief Goosen and claimed his second PGA TOUR Champions victory.

Successfully defended his title at The Ally Challenge, defeating Ernie Els in a sudden-death playoff for the 2025 crown. It was his second win of the 2025 season and third win overall on PGA TOUR Champions. Became the first multi-time winner of The Ally Challenge (2024, 2025). Led the field in driving distance (319.2 yards) and ranked 77th (out of 78) in driving accuracy (11-of-42).

Closed the season with a victory at the Charles Schwab Cup Championship, also capturing his first Charles Schwab Cup in the process. Carded scores of 64-68-65-67 to post 20-under and finished two strokes ahead of Steven Alker, who entered the week atop the Charles Schwab Cup standings. Became the fourth player to win the Charles Schwab Cup Championship and the Charles Schwab Cup in the same year. It was his third win of the 2025 season, and fourth win overall on PGA TOUR Champions. Entered the season finale ranked No. 3 in the standings and controlled his own destiny, with a victory in the tournament guaranteeing the Charles Schwab Cup (regardless of how any other players finished).