A bogey, double-bogey, par finish at the Senior Open left the 55-year-old Scot trailing first round leaders Kirk Triplett of America and Thailand’s Thaworn Wiratchant by six shots.
After finding sand on the 16th, Monty came to further grief at the notorious Road Hole when he was forced to play out of the bunker sideways for the second time and shed two shots in the process when he carded a six.
Monty, runner-up to Tiger Woods in the 2005 Open at the Old Course, had earlier looked imperious as he ticked off five birdies in the first 11 holes before shedding a shot at the 12th.
He eventually had to settle for a one-under-par 71 while another Ryder Cup-winning captain, Paul McGinley avoided such frustrations when he posted his lowest score at the home of golf.
The Irishman compiled seven birdies and a single bogey for a 66 to share third place on a day when the sun shone brightly and large numbers of spectators enjoyed the spectacle of the game’s ageing legends rolling back the years in some style.
McGinley, 51, pictured, could hardly contain himself as he waxed lyrical about his surroundings. “Playing the Old Course on a day like this is just fabulous,” he enthused. “It’s magical and mystical and if you can’t enjoy days like this irrespective of your score, you’ll never enjoy golf.
“But the wind was really tough on the back nine and that’s where the teeth in St Andrews is, but if you love golf and the history and all it stands for, this is the place to be.”
McGinley’s undiminished competitive spirit is the reason he still loves to play the game, but he also has other commitments and goals that have curtailed his tournament involvement to seven events last year and three so far this season.
“I’m doing lots of things with different companies, leadership talks, public speaking at London Business School where they made me a fellow,” he explained. “I’m also on the board of the European Tour and I’m hosting the Irish Open next year.”
The crowds were spoiled for choice when it came to deciding which group to follow, but the trio of Tom Watson, Bernhard Langer and Miguel Angel Jimenez was irresistible for many and they were not disappointed.
Defending champion Langer, eyeing a fourth Senior Open title, carded a 67, one lower than Jimenez, while Watson just missed out on shooting his age with a flawless 69.
It has been 34 years since Watson and Langer played together in an Open at St Andrews, but it was as if time had stood still yesterday as they reminisced over the joint second-place finish behind Seve Ballesteros in 1984.
Langer said: “It’s always a pleasure playing with Tom. He’s a great gentleman and a fantastic player and I think we fed off each other. I told him on the 18th that he’s still hitting a lot of solid shots and you can see why he won so many titles around the world.
“You can always learn from him. He’s a fantastic wind player and he’s got a great mind. He never gets down on himself and is always very positive.”
Watson reflected: “I’m happy with that. I played a lot of quality shots, my favourite being my 3-iron on 17 when I hit it exactly 200 yards to the top of the table, which is a great accomplishment at the Road Hole.
“I had no shanks or three putts to finish, unlike my last round here in the Open and I had a putt from 25 feet at the last to shoot my age and left it short.
“I’ve been practising my chipping and long putts from 80 feet and I didn’t have a five on the card today for the first time in a couple of decades.”
Having being forced to withdraw from last week’s Open Championship at Carnoustie, American John Daly returned to the fold only 12 days after undergoing a procedure to have bone marrow transferred from his hip into his right knee in an effort to cure a troublesome injury.
It was hardly the best preparation for a return to the scene of his 1995 Open triumph but the 52-year-old American still a managed to register a 69 for a share of 17th place.
He said: “I felt it about the seventh or eighth hole, but my doctor told me it’s going to take two to six weeks for the burning to get out of the hip.”