The Scot finished in third spot 16 years ago, just three strokes adrift of the eventual winner Tom Kite. Monty led the pack after the second day at Pebble Beach Golf Links but after a disastrous third day's play saw his hopes of a major crown dashed. He shot a 79, nine strokes more than the day's front runners Nick Faldo and Joey Sindelar to leave himself five behind leader Kite. Monty grasped back to within three strokes of Kite on the final day, but it was not enough to over-ride his miserable third day showing.
Montgomerie went one better two years after finishing third. He came in second behind first-time winner Ernie Els after a dramatic final day three-way play-off. At the end of 72 holes Monty locked horns with Loren Roberts and Els who finished five-under at Oakmount. But three double-bogeys cost the Scot a place in the history of the competition once more.
Second-placed again, Montgomerie came agonisingly close just one off of champion Els, who scooped his second US Open title at the expense of his Scottish rival. Monty opened a comprehensive six-stroke lead over the eventual South African winner but shooting a 76 on two day saw him playing catch up once more. Els only out-scored Monty on one of the competition's four days yet his maiden major crown continued to prove elusive.
This is probably regarded as Montgomerie's biggest US Open career choke after he holed a 75-foot birdie putt on the 17th. This put the Scot in the ascendancy but he double-bogeyed on the final hole on the last day at Winged Foot to surrender his grasp. Monty and Phil Mickelson both collapsed at the last allowing for Australia's Geoff Ogilvy to steel in for the nation's first title in 25 years.