When considering Europe’s greatest ever Ryder Cup player, there are a handful of obvious candidates.
Sergio Garcia and Nick Faldo stand as the top points scorers, while Ian Poulter’s near-supernatural ability to raise his game every two years is unparalleled.
And while Colin Montgomerie never won a major, he’s certainly in the conversation for Europe’s greatest player, with a better points percentage than Garcia, Faldo and Poulter and a remarkable record of never losing a singles match.
In fact, nobody in Ryder Cup history has taken more points in singles than Monty. Not Garcia, not Faldo, not even Poulter.
Although he was an excellent amateur golfer, twice playing in the Eisenhower Trophy and Walker Cup, his record in neither tournament would lead anyone to believe he was destined to be a European great.
In his eight European matches at the Walker Cup, Montgomerie won just twice.
But four years later, his luck in team events against the United States would change.
Turning pro in 1988, Montgomerie would win Rookie of the Year, before winning the Portugal Open by 11 shots in 1989.
The Ryder Cup would come too soon that year, but in 1991, Montgomerie qualified second on the European points list, to be named as one of five rookies set to take part on the ‘War on the Shore’.
It was a hostile introduction to the Ryder Cup for Monty, but it’s something he’d quickly have to become accustomed to.
Montgomerie was 1-1-0 heading into Sunday’s singles. With the competition tied at 8-8, Monty went out third, taking on Mark Calcavecchia. If he wasn’t already aware of it, Montgomerie was about to see first-hand what the Ryder Cup can do to a man.
Calcavecchia was cruising; 5UP thru 9, the Americans looked to have an early point on the board.
Montgomerie clawed one hole back but was down dormie 4 and staring down the barrel. After Calcavecchia lost 15 and 16 to keep the match alive, Montgomerie faced a testing tee shot in a howling wind, desperately trying to find the putting surface. He failed, and that should’ve been that.
But Calcaveccchia, who would’ve prompted a handshake with an accurate tee shot, also found the water. The American still had a two-footer for double bogey which would have won the match, and Montgomerie later recalled that he was about to concede, but decided to let his opponent hole out. Calcavecchia failed there, too.
Montgomerie won the 18th hole to secure an almost impossible half point, while Calcavecchia was left utterly distraught. He left the course to go for a walk on a nearby beach, was in floods of tears, and rumours circulated that he was physically sick.
The Ryder Cup was not for the fainthearted.
Montgomerie returned two years later, armed with a new partner. Nick Faldo was never the most popular player amongst colleagues on either side of the pond and the same was true of the Ryder Cup teams he played on, but in Montgomerie he’d found a useful foil.
Monty wasn’t the type to be put out by Faldo’s aloofness, nor intimidated by his stature in the game, and together they took 2.5 points from a possible 4 to give Europe a slender 8.5-7.5 lead going into Sunday.
Montgomerie went out third again, and while he secured his point, Europe failed to win any of the bottom seven matches, and would lose 15-13.
Only Ian Woosnam scored more than Mongomerie’s 3.5 points that week, but Monty’s wait to win the Ryder Cup went on.
Come 1995, plenty had happened to Montgomerie since the last Ryder Cup, being beaten in play-offs at the 1994 US Open and the 1995 PGA Championship, and with the waning powers of Seve Ballesteros, Faldo and Woosnam, Monty was Europe’s star man having won the Order of Merit the last two years and being weeks away from making it a hat-trick.
The marquee pairing of Faldo and Montgomerie from two years prior lost both matches on Friday, winning on Saturday morning before being split up on Saturday afternoon.
Monty went into Sunday’s singles having hugely underperformed, taking just one point from three matches. Monty was sent out seventh, beating that year’s Masters champion Ben Crenshaw 3&1.
9-7 down on enemy territory, Montgomerie kept blue on the board on Sunday as Europe won seven of the 12 singles matches to take the Ryder Cup back across the Atlantic by the narrowest of victories.
After the European supremacy in the late 80s with the likes of Faldo, Langer, Olazabal, Ballesteros and Woosnam, 1995 ushered in a new era, reminding Europe they could not just win Sunday’s singles, but do it on American soil to win the Ryder Cup. And winning the Ryder Cup away from home is no mean feat; since Europe joined the competition in 1979, the scoreboard reads 15-6 in favour of the home sides.
By 1997, Montgomerie had achieved almost everything there was for a European golfer to achieve in the game. He’d topped the Order of Merit in three straight years, reached number two in the world and finally had a Ryder Cup win to his name. He hadn’t won a major – adding another runner up at the 1997 US Open – something that would elude him throughout his career.
Although still not a major winner, the Scot had a target on his back in 1995 as Europe’s number one golfer, but ahead of the 1997 contest, he made the bullseye that bit bigger.
Montgomerie did little to ingratiate himself with American crowds, with a near-permanent frown etched on his face, which quickly turned into a scowl at the slightest inconvenience, a scowl many a photographer and spectator found themselves on the receiving end of.
With a rather grumpy demeanour as well as being Europe’s best player, Montgomerie would be the primary target for heckles from the Americans and did little to help his cause with comments made prior to the 1997 edition.
What was once a friendly competition had become more hostile over the years, certainly in 1991 with the ‘War on the Shore’, and while the Ryder Cup was still played in good spirit, there was certainly more animosity than there once was.
Monty aimed a series of barbs at a handful of the Americans, but got a little too personal when suggesting that Brad Faxon’s divorce might mean he’s not all there mentally for the competition, riling a number of his opponents.
Montgomerie would later apologise and insisted that the remarks were taken out of context, but as far as his play went that week he was almost flawless. Monty lost his opening match but won the next three.
On the off chance that Europe’s 10.5-5.5 lead would be wiped out on Sunday, Monty was sent out last as the anchorman. Europe’s safest pair of hands, just in case they were needed.
And they were.
The USA won seven of the first 11 matches before eventually getting to the golden 14 points needed to retain the cup.
Montgomerie ensured he couldn’t lose his match, but with Europe at 14.5 points and the win now mathematically secured, captain Seve Ballesteros conceded Scott Hoch’s 15-foot putt on the 18th green, meaning Monty lost the hole and halved the match.
Unhappy at the concession, but still unbeaten on Sunday.
Things ramped up significantly in 1999 at Brookline in front of the most hostile crowd the event had ever seen.
Montgomerie was still majorless, but had further cemented his place as Europe’s best golfer with two more Order of Merits. And, boy, would Europe need their best golfer in 1999 against the all-star American team.
David Duval, one such all-star, claimed that with the event getting bigger and more financially lucrative, players should start being paid. It wasn’t a popular opinion, and Montgomerie, never one to miss an opportunity, fired back by saying that no European would ever want to be paid, and that the Ryder Cup should be played for flags, not money.
The well-fancied Americans found themselves 6-2 down after the first day, with the fans realising they needed to play their part.
With Hal Sutton holing a lengthy birdie putt, Montgomerie sternly waited for the prolonged cheers to die down. When they eventually did and he stood over his putt, a heckler called out.
Monty backed off, regained his composure, and holed the putt. Montgomerie wasn’t one for showing emotions – not positive ones anyway – and rarely acknowledged the existence of the crowd, but made an exception on this occasion, fist pumping in celebration.
Captain Mark James had fielded seven rookies; Montgomerie and Jose Maria Olazabal were the only two players with more than one Ryder Cup to their name, but the hugely unfancied Europeans found themselves closing in on victory.
Monty played all four sessions with rookie Paul Lawrie, taking 2.5 points as Europe led 10-6 going into Sunday.
But what could’ve been one of Europe’s finest hours turned into its darkest. One by one, red scores were appearing on the leaderboard as Europe’s four-point advantage ebbed away.
To make his day more difficult, Montgomerie, who’d considered himself immune to calls from the gallery, was getting both barrels from Boston’s finest. So much so that his dad didn’t even reach the back nine due to the abuse his son was receiving. Even opponent Payne Stewart stepped up and said he’d sort any fans out who crossed a line, while Monty had no qualms about getting people ejected.
Montgomerie, who’d previously claimed he’d love to be sent out last on Sunday – arguably the most important position – changed his tune after the nerve-shattering conclusion in 1997. And though he was sent out third last, his match was the last on the course.
If there was a positive to take, however, it was in Stewart’s sportsmanship, in conceding the final hole to his opponent, ensuring Montgomerie didn’t have to go through the consequences of losing the 18th and halving his match.
Back on familiar ground at the Belfry in 2002, Montgomerie was now Europe’s second oldest player behind the 45-year-old Bernhard Langer.
Ian Woosnam sent the duo – with a combined 61 Ryder Cup matches to their name – out in the first three sessions where they’d take 2.5 points.
Langer was rested for Saturday’s four-ball when Monty partnered up with Padraig Harrington; the pair winning 2&1 as Europe went into Sunday level at 8-8.
Woosnam put his best foot forward for the final session; Colin Montgomerie, unbeaten in his four matches, out first for Europe.
And as he did so often, Montgomerie delivered, and delivered in style. The mental aspect of seeing blue – or red – on the board on Sunday for the players going out later can’t be understated, and how much of a relief if must have been to see that Montgomerie had won his match 5&4 to get an early point in the bag.
Europe won 15.5-12.5; revenge for 1999, with the cherry on top for Montgomerie being that he finished as Europe’s top scorer for the third straight Ryder Cup.
By 2004, Montgomerie’s best years were behind him, needing a pick from captain and old partner Langer, but he was sent out first on Friday with Harrington to take on the marquee pairing of Tiger Woods and Phil Mickelson. Europe won 2&1, with Monty going one better with a 4&2 win that afternoon.
Europe led 11-5 going into Sunday and the result was virtually assured. There was one thing left for Montgomerie to tick off his bucket list as a Ryder Cup player, and that was to hole the winning putt.
Technically he’d secured the winning point in 1997, but Europe had already reached 14 points to retain the cup. In 2004, he’d secure the decisive point, beating David Toms on the 18th hole.
A turnaround in form saw Montgomerie qualify for the team automatically at the age of 43 having won an eighth Order of Merit in 2005, and while Monty would only take one point from his first three matches, he was sent out first again on Sunday, to play Toms again, and win again.
Montgomerie finished his Ryder Cup career as Europe’s third highest points scorer (since overtaken by Garcia and Westwood), with an unbeaten singles record of 6-0-2.
He’d even have the honour of captaining Europe in 2010, beating the USA in a dramatic Monday finish, which Montgomerie called the ‘proudest moment of my career’.
Monty might have never won a major, but he was on the winning side in five Ryder Cups, going on to captain the side to victory in Wales in 2010.
And in the end, that was more than enough.