“His first five holes are most important for him for the tournament,” said the Scot, who finished second to Woods in 2005, when the world No 1 at the time followed up a runaway victory on the Old Course five years earlier.
“He has to be a couple under, which most of the field will be at that stage by birdieing one of the first three holes and the (par-5) fifth. If he can do that, then he will get the juices flowing and get the competitiveness back.
“He will start to think he can do it and there is no reason why he can’t as he putts as well as anyone when he gets it going. He knows his way around the greens like nobody else. He has won here twice, easily.”
The prospect of Woods being a challenger this week looked slim when he made an early exit from the US Open at Chambers Bay last month following dismal rounds of 80 and 76, having slumped to a worst-ever 85 in the Memorial Tournament prior to that.
However, the 14-times major winner handed himself a much-needed boost when he shot four rounds in the 60s in his most recent outing, a joint-32nd finish in the Greenbrier Classic a fortnight ago.
“Tiger can be a factor, of course he can,” insisted Montgomerie. “His last round was bogey-free and, if he’s two under par after five on Thursday, he’ll get the bit between his teeth and give it a go.
“If there’s one course that suits the fellow, this is it. He can’t hit the greens from where he has been hitting it. But, at St Andrews, he knows he can hit it miles off line and still be ok. He knows his way around this place and knows what he’s doing. I didn’t lose in ’05, he won.”
Woods led from wire-to-wire on that occasion. He opened with rounds of 66 and 67 to lead by four shots from Montgomerie at the halfway stage. Jose Maria Olazabal closed the gap to just two shots after the American shot 71 in the third round before a closing 70 saw Woods win by five shots from the Scot.
“I had done my job – I had beat the rest of them,” recalled Montgomerie. “Tiger was the best in the world by a mile. After finishing second to someone like that, you stand up and say, ‘thank you very much’. Nothing wrong with that performance.”
On playing with Woods on the penultimate day, he added: “He had a couple of loose drives but you are always aware of what he is doing. You could always sense, especially on the back nine into the wind, that he had so much power compared to everyone else. He could get by trouble that I was trying to feed my way through.
“These days are gone now and he is not the longest by a long, long way – and he is not the straightest by a heap! These days are gone and he has got to get the putter going. At St Andrews you are going to hit 15 greens in regulation. If you don’t then you have played really badly as they are big enough.
“Really, it is a putting competition and always has been there. He was the best putter in 2000 and 2005 by a mile. That is why he won. He used to never miss a putt. It has deteriorated and he lost confidence.
“But he might get that confidence back over the first five holes. His last round was bogey-free. He hasn’t played a bogey-free round for a long time. He stands on that first tee and he is going to hit that first fairway (the widest in the game) – if he doesn’t do that then he is in big trouble.”