Who has had the most runner-up finishes at the Masters?

There is perhaps nothing more agonizing for a player than finishing runner-up — especially at a major championship. With so many perks at stake — money, world-ranking points, exemptions and of course, the life-long prestige that accompanies a high-level win — falling just short can be supremely painful.

But what about players who have experienced that feeling more than once? Phil Mickelson famously owns six runner-up finishes at the U.S. Open — the only major championship he has yet to win to complete the career grand slam.

Mickelson’s single-major runner-up total is surpassed only by Jack Nicklaus, who had an eye-popping seven runner-up finishes at the Open Championship between 1964 and 1979. Nicklaus, who boasts a record 18 career major championship wins, has an incredible 19 total runner-ups at the majors.

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So, which player has been disappointed the most at the Masters?

Though the answer is that it’s a tie between three players, there is one player who is indisputably the most disappointed one: Tom Weiskopf. Weiskopf finished second at the Masters four times over the course of his career, and never won at Augusta.

Nicklaus, too, finished second at Augusta a total of four times. Fortunately, he also has a record six green jackets to ease the sting.

The third player to have four runner-ups at the Masters is Ben Hogan, who also won twice.

When it comes to players who have finished second three times, it’s a five-way tie that features some of the game’s greatest players: Greg Norman, Tom Watson, Johnny Miller, Raymond Floyd and Tom Kite.

The number of players who have managed to finish runner-up at the Masters twice is even longer. Check out the full list of players with the most Masters runner-up finishes below.

Players with the most runner-up finishes at the Masters

Ben Hogan (4)
Jack Nicklaus (4)
Tom Weiskopf (4)
Raymond Floyd (3)
Tom Kite (3)
Johnny Miller (3)
Greg Norman (3)
Tom Watson (3)
Seve Ballesteros (2)
Harry Cooper (2)
Ben Crenshaw (2)
Ernie Els (2)
Retief Goosen (2)
Ralph Guldahl (2)
Lloyd Mangrum (2)
Cary Middlecoff (2)
Byron Nelson (2)
Arnold Palmer (2)
Gary Player (2)
Sam Snead (2)
Jordan Spieth (2)
Craig Wood (2)
Tiger Woods (2)