It was the third year running that the over-50s title had fallen to Montgomerie, who achieved the same feat in the PGA Championship on the main circuit, between 1998 and 2000, and he now has ownership of this particular trophy after the sponsors decided to hand it over permanently to the 52-year-old.
However, it was only won on this occasion after Drummond suffered the cruellest of conclusions in his brave bid to finally become a winner at the highest level after 490 starts on the European Tour and 125 on the Senior circuit.
Playing the last, the 58-year-old had that elusive victory in his grasp, holding a two-shot lead after Montgomerie, the overnight leader, had dropped a shot at the 17th to fall back to four-under-par.
However, Drummond three-putted the final green - he closed with 69 for a five-under-par total of 211 - and, unfortunately for him, the glimmer of hope he offered Montgomerie was to prove costly.
However, that fatal glitch on the final hole provided the chink of light which his much decorated rival needed.
Knowing that he needed a birdie to force a play-off, the three-times Senior major smashed a 270-yard drive up the last, followed that with a delicate chip to two feet and rolled in the putt for a last-round 71.
The first play-off hole was halved in par-4s, with Montgomerie taking a conventional route and Drummond holing from five feet for a par after overshooting the green. Back the pair of protagonists went to the 18th tee and Drummond had to pitch from behind the green once more to make his par.
However, Montgomerie needed no second invitation and his 18 footer unerringly found the centre of the hole. Drummond’s shoulders slumped and even his conqueror seemed almost apologetic at ending his countryman’s title dream after 28 years on the European and Senior Tours.
“How can you not feel sorry for someone who played the difficult holes so well?” admitted Montgomerie afterwards. “The 15th, 16th and 17th are all good, difficult golf holes and Ross did all the difficult stuff very well. You have to feel sorry for him getting so close, but I am sure this will give him a lot of confidence to go forward.”
Achieved despite an opening 73, the success in front of a last-day crowd of more than 7,000 was Montgomerie’s seventh since he joined the over-50s ranks just over two years ago
“I always thought my performance at Wentworth in 1998, 1999 and 200 was the best I could do,” he added. “Winning three times in a row was really hard on The European Tour, so that was probably the ultimate accolade in my golfing career. But I have to say this comes extremely close to emulating that.
“I came here to Woburn with a lot of pressure on me as the favourite to win and it’s sometimes difficult and harder to achieve when something is expected of you. And today proved that point. I was having some putting issues coming in and three putted the tenth and17th and missed a ‘gimme’ for birdie at the 15th.
“Then I heard that Ross had bogeyed the 18th and it gave me a chance to birdie the last to get into a play-off. That wasn’t easy, knowing you need a birdie and achieving it to get into a play-off. Then I managed that birdie on the second play-off hole. I got very fortunate to come away with a win.”
Drummond, a four-times Scottish PGA champion, picked up a consolation cheque for around £32,000. He finished sixth on his rookie Senior Tour season in 2007, helped by two runner-up efforts, and is up to ninth on this year’s money-list after this outstanding display.
“It’s very hard to take” admitted the Prestwick-based player. “I’ve never won out here in almost three decades and I should have taken the chance. That hurts a lot.
“I really ought to have wrapped it up in regulation play, but my awkward yardage at the 18th meant I needed a gap wedge and the ball spun back about 30 feet from the hole. I mishit the first putt and didn’t execute the second one from three and a half feet. There’s not much more I can say.”
Elsewhere, Craig Lee moved into the safety zone in the battle for European Tour survival as Englishman Lee Slattery claimed victory in the M2M Russian Open.
Joint-second heading into the final round at Skolkovo Golf Club on the outskirts of Moscow, Lee never really got into the shake up after starting with a bogey.
He recovered from that early blow with back-to-back bogeys at the third and fourth before a dropped shot at the ninth took him out in level-par.
The 38-year-old Stirling man got into red figures again with a birdie at the 12th only to give that back three holes later and signed for a closing 71.
On 11-under par, he finished joint-eighth - the same position the former Tartan Tour played ended up seven days earlier in the Czech Masters.
Lee earned around £16,500 for his latest effort and has picked up close to £32,000 in the last two events, lifting up to 108th - two inside the safety line - on this season’s money-list.
With seven regular events remaining before the lucrative ‘Final Series’, David Drysdale has also boosted his hopes of avoiding a visit to the Qualifying School.
A third successive 69 saw him finish joint-14th on nine-under, earning a cheque for just under £11,000 to move to 114th on the rankings.
Facing a bigger challenge over the final weeks of the campaign to hang on to a card is Chris Doak, though he’s showing signs of being able to achieve that target since he linked up with his new coach, Kevin Craggs.
Doak finished joint-17th - his best effort of the season in a stroke-play event to move to 155th in the Race to Dubai. Scott Jamieson, the first-round leader, finished alongside his compatriot on eight-under. It wasn’t the result he was looking for after opening with a 65, but the Glaswegian is 97th on the rankings so can try and push hard over the coming weeks to make the ‘Final Series’.
Slattery’s hopes of competing in that have certainly been boosted after a second European Tour triumph catapulted him to 66th in the Race to Dubai.
The 37-year-old started the final day with a two stroke advantage. He began in impressive fashion with a birdie at the first hole, but he soon found himself over par with bogeys at the second and sixth holes.
Slattery dug deep, however, and as a host of challengers began to emerge, he picked up three shots on the way home - including a hugely important holed chip at the 17th – before sinking a knee-jangling three footer at the 18th for a par which earned him a two under 69, a 15 under total and a first win since the 2011 Madrid Masters.
“Going back over the last year and a half off the golf course, I’ve got married, had a kid and moved house. My wife’s dad is also very ill as well, so this is for him,” he said.
On the Challenge Tour, tartan trio David Law, Jack Doherty and Peter Whiteford all finish joint-ninth as Australian Scott Aenold won the Gordon Golf Open in France.
And, in the Helsingborg Open on the Ladies European Tour, Kylie Walker was top Scot, though a closing 77 saw her slip to joint-21st behind Dane Nicole Broch Larsen.