Montgomerie came to the Target World Challenge two years ago believing his worst days were behind him. Having started the season at No. 81 in the world, he challenged Tiger Woods at St. Andrews and at a World Golf Championship, building blocks that helps him turn around his fortunes and finish 2005 at No. 9 in the world.
His plan was to stay in the top 10, if not move even higher.
But when he arrived at Sherwood Country Club as a substitute for the injured Davis Love III, the 44-year-old Scot was No. 56 in the world and in dire need of another comeback.
He is not eligible for the Masters. Of greater importance, this is a Ryder Cup year.
'I've got a big year ahead,' he said Wednesday. 'Obviously, there's a marriage in April -- trying that again. And obviously, I've got to get my act together in playing terms to get back into the Ryder Cup scene. I'd like to participate again. I've played in the last eight, and I'd like to make that nine.
'The standard is improving all the time, and I'm getting older.'
The year hasn't been a total loss. He won the European Open in Ireland for his first victory in 18 months and the 31st of his European Tour career, giving him one more than Nick Faldo. And he finally helped deliver a World Cup to Scotland, teaming with Marc Warren to hold off the Americans last month in China.
Montgomerie came close to winning the Target in 2004, taking a two-shot lead into the final round and finishing three behind the tournament host. He is part of a 16-man field that includes Woods, the defending champion, Jim Furyk, Vijay Singh, Padraig Harrington and the ever-present Fred Couples.
It is a holiday for most, especially with a $5.75 million purse and $1.35 million going to the winner.
But he knows the real test starts next year.
Montgomerie made his Ryder Cup debut in 1991 and has become Europe's best player over the years. The putts that he can't seem to make in the majors never seem to miss when he puts on a team uniform.
He has earned 23 1/2 points in the Ryder Cup, second only to Faldo and Bernhard Langer. Montgomerie has never lost in singles, and one more singles victory would break the Ryder Cup record he shares with players such as Faldo, Billy Casper, Arnold Palmer and Sam Snead.
But that kind of history won't guarantee a spot on the team at Valhalla in September. Of the eight times he has played in the Ryder Cup, he has been a captain's pick only once, in 2004 by Langer.
'Even if I get to 12 or 13 on the list, or whatever the case may be, I might get picked again,' he said. 'Nick knows the situation, and he's aware of it. And so am I.'
Faldo didn't show much love earlier this fall at the Seve Trophy, where he told British reporters that Montgomerie didn't appear to be a team player because he didn't go to the meetings.
Montgomerie said he has spoken to Faldo and everything is fine. He's more concerned about his game.
'I've putted particularly poorly those last two years,' Montgomerie said. 'I won the Order of Merit in 2005 and I was eighth in the world. Now I'm 50-something, and it's far too low. I've missed far too many putts that the competition are holing, and I've got to get back to putting. It's just a couple of putts a round, but that's eight shots a tournament. If you take eight shots off of every tournament I play, I'm winning four or five a year, at least.'
Montgomerie has never been known as a great putter, except one week every two years in the Ryder Cup. He could get by as a decent putter because his swing has been so sound for so long. Now, that's no longer the case.
'I could get away with putting average,' he said. 'But not now. The standards have improved. I've got to putt well to win.'
And this tournament, even that might not be enough.
'I've done OK here,' Monty said. 'I was two shots ahead one year, but I don't know. Some fellow beat me. I don't know his name. He's quite good, has potential. So he won. He'll probably win again.'
Woods is playing for the first time in 10 weeks, not since Sept. 30 at the Presidents Cup. He was on the putting green after his pro-am round, hitting putts with one hand, the blade positioned between two tees. He made most of them.
Small wonder that Woods has won his tournament three times.