It would have been even more painful for the Scot, however, if he'd found himself in the shadows once again when The Open Championship celebrates its 150th anniversary at St Andrews in five weeks' time.
He was runner-up to Tiger Woods the last time the game's oldest major was held at the home of golf in 2005.
And, in the year of his Ryder Cup captaincy, it would have been galling for Montgomerie to have seen a run of playing in 20 consecutive Opens since making his debut at St Andrews in 1990 come to an end.
His hopes of continuing that run looked slim when he posted a one-under 69 on the Old Course at Sunningdale yesterday in the opening round of the European International Final Qualifier.
But the eight-time European No 1 roared up the standings in the afternoon with a course-record equalling eight-under 62 on the New Course to secure one of the ten St Andrews spots on offer with a nine-under 131.
Monty, who shared second place with fellow Scot Andrew Coltart, finished two shots behind Irishman Shane Lowry, who topped the leaderboard with 129.
Looking forward to his return to St Andrews, Monty said: "It's a special place, there's no question, and to finish second there to the best player that's ever played the game means you go with a bit of confidence. It's home, I've got good support and I'm looking forward to it."
The Scot, who bagged five birdies in his last seven holes, feared he had blown his chance when he put his approach to the last in a bunker.
"I thought the last was a par-4 so I was very concerned when I went in the bunker," he revealed. "If I didn't get up and down I thought I would drop a shot and be in a play-off. I didn't appreciate the last was a par-5 but I ended up taking four and making a birdie so it didn't matter."
His round equalled the record set by Graeme Storm in the same event a year ago.
Lowry, only one-under par at the turn during his morning round, started for home with six successive birdies and by pitching to 18 inches at the 425-yard 17th he was able to equal the joint lowest score of Nick Faldo's European Tour career. "I've been struggling on the greens and confidence was a bit low, so I changed my putter this morning," commented Lowry. "After nine holes I said to my caddie I'm going to have to be patient and it certainly paid off.
"St Andrews is going to be great. I said at the start of the year it's one tournament I wanted to play."
Joint-fourth were Northern Ireland's Gareth Maybin and Dane Thomas Bjorn – second to Woods at St Andrews in 2000 and to Ben Curtis at Sandwich in 2003. One stroke further back were Welshman Bradley Dredge, Spanish duo Ignacio Garrido and Jose Manuel Lara and also Argentina's Tano Goya.
That left six men on six-under with one place left, but that instantly became five because South African James Kingston had already decided to head off to Heathrow for a flight to Botswana.
The tenth spot went to Marcel Siem, the German who led the Wales Open with a round to go, with a birdie at the first extra hole. Welshman Jamie Donaldson, Dubliner Peter Lawrie, France's Gregory Bourdy and Swede Patrik Sjoland failed to match him.
Among those who missed out were Darren Clarke, Paul McGinley and 17-year-old Italian Matteo Manassero, who would have been in the play-off if he had made a 12-foot eagle attempt on the last.
The young Italian, now a month into his professional career, finished in a tie for 13th at Turnberry as the reigning British amateur champion and came joint-36th at The Masters in April – the best finish by a European amateur at Augusta for 73 years.
Peter Whiteford (138), Scott Drummond (139) and Richie Ramsay (140) all failed to make the qualifying grade while Alastair Forsyth, well in the hunt after an opening 65, slumped to a 76 and missed out with a 141.
Stephen Gallacher, with a trio of top-ten finishes in his past three European Tour events, withdrew after taking a 7 on the second hole of round two which put him out of the picture.
"The 7 really knocked the stuffing out of me and I was running on empty after that," he said.