I used to measure the passing years by my annual interviews with Colin Montgomerie at an Open Championship.

Every year it was the same – be it St Andrews, Troon, Royal Lytham, Birkdale – the question always posed by reporters was: "Can Monty land a big one?" Alas, he never could.

He is (roughly) the same age as me, and, worryingly, it was even claimed by one or two that we physically resembled each other. And so, perversely, at each Open, I would almost psychologically measure how well I was doing by how well Monty was doing.

Sad to relate, then, that this is a pretty significant time for me. Monty has just turned 50, he is now officially a "senior" golfer, and this weekend he is in Pittsburgh, Pennsylvania, doing what he once vowed he would never do: chasing a prize on a senior tour, in this case at the Senior Players Championship on the USA's Champions Tour.

You cannot miss the delicious irony in all this. It is said that on Monty's gravestone it will be written, "He Never Won A Major", but he now has the chance to win a stack of them – or at least senior ones. Would they still count? They would to Monty.

The "burly Scot" (that's copyright) is planning to spend at least threequarters of every playing season in the immediate future in the USA, a place where Monty has not always curried favour with indigenous golf fans.

Time upon time back in his 1990s heyday he was goaded, heckled or sent up by Americans who tended to view him as a sort of Billy Bunter figure who had blundered on to the golf scene.

In Ryder Cups, Montgomerie soon showed the Yanks what steel and resolve were all about – in eight outings he was unbeaten in the singles – and won a grudging respect across the USA for that.

Yesterday, though, given that Monty at 50 is going to be seen a whole lot more in the USA, I sought out an American voice to put his reputation over there in context. "I've always liked Monty – he makes for easy copy and good quotes much of the time," said Scott Michaux, a prize-winning sports columnist on the Augusta Chronicle.

"My sense is that, at one time, he was such an easy target for American crowds as he came over as being a bit smug and thin-skinned. Once Monty made it apparent that he let everything get to him, the galleries over here duly obliged by piling in.

"But he was certainly respected for his talent. The 'Be Nice To Monty' campaign at the US Open at Bethpage in 2002 was a success. He got no grief, either, at Winged Foot in 2006, though he derailed himself there in any case.

"I guess the Ryder Cup probably brought out the best in Monty, and some of the worst in USA fans hoping to get under his skin."

Montgomerie himself remains a bit of a contradiction. The man who topped the Order of Merit on the European Tour a record eight times has had just two top-10 finishes in his last 100 outings, yet maintains that his game "is in good order".

But here's the real point: seniors golf can be a jackpot for older players, it can completely rejuvenate their careers.

Just ask Roger Chapman, a relatively unsung Englishman, who landed the US Senior PGA and US Senior Open titles last year; or Bernhard Langer, who has mopped up $10m in five years on the Champions Tour.

Monty, if he can remain focused and reasonably fit, has the chance to do some serious winning and cleaning up in the years ahead.

"I've basically got the opportunity, at 50, to start again – and that doesn't often happen in sport," he says. "I've now got three tours to aim at: the European Senior Tour; the Champions Tour in America; and the regular European Tour, which I still want to compete on.

"In senior terms I'm looking forward to a new career. I used to think 50 was old but it now seems not that bad. It's funny, because I always felt, and I said it openly, that I wasn't really interested in playing senior golf. But now I've reached 50 and found that I'm as fit – well, I've never really been fit – but as fit as I've ever been.

"It is the competitiveness, the competition, which has driven me forward to play seniors golf. I'm not ready to stop competing. I still feel hungry for success. And I don't just want to compete – I want to contend."

Montgomerie says he will play around 30 tournaments a season over the next few years: 20 on the Champions Tour; seven on the regular European Tour; and maybe three on the European Seniors Tour.

So America, where the Champions Tour total prize fund currently stands at $52m, is where his sights are set. Dunning, the snug little Perthshire town where Montgomerie lives, will scarcely have known such a jet-setting resident.

"It was a couple of years ago that I changed my mind and decided I would play seniors golf," says Monty. "I thought, I'm better off doing what I do best, which is play golf. Everyone gets older but I've remained hungry for success, and I think that's important.

"Recently I've been playing against guys who have been younger than my children, so you think, 'hang on a minute, this isn't a level playing field'. I'm playing against guys aged 23 or 24 who hit the ball a mile. So let's get a bit of parity back, in that sense. In fact, I'll be a rookie again on the senior tours."

Monty is playing Pittsburgh this weekend – he hit a first-round, one-under-par 69 that left him four off the lead and – then the US Senior Open in Nebraska in two weeks' time. That will be followed by the British Senior Open at Birkdale in late July.

And so it can be asked again . . . can Monty land a big one? "I'm under no illusions about how good the standard is in senior golf," he said. "Bernhard Langer is dominating it right now, and there's Freddie Couples, David Frost, Kenny Perry, Tom Lehman . . . the list goes on.

"There are good players out there. But, yes, it's about time I won a major championship, so let's hope that one might be in offing."