Woods barely featured this year outside of playing in three of the four majors as he continued to battle injury problems, but he returned to action alongside Rory McIlroy in The Match over the weekend and also intends to partner son Charlie in this week's PNC Championship.
As for next year, Woods has already admitted he is only really targeting the majors and one or two other events, but Montgomerie reckons his emotional appearance in the 150th Open at St Andrews in July would have been the perfect time for the 15-time major winner to call it a day.
"That was the time," Montgomerie said during a recent appearance on the Bunkered podcast.
"Stand on that bridge, start waving, and everyone goes, 'So, is that it?' 'Yeah, it is.'
"It would have been a glorious way to go. The stands were full, the world's TV cameras - from all continents - were on him, he's walking up there on his own, tears were in his eyes, obviously, you can't beat that walk.
"I've done it myself. When the stands are full, you cannot beat that walk. I tell you what, that is a special, special arena. It's a theatre. That was the time for Tiger to say, 'OK, I bow out. Why go on? Go out at the top. It's something that very few can do."
Woods had planned a much busier 2022 than he ended up having, but his body had other ideas.
He made a surprise return at the Masters in April, and while he emerged with a credible top-50 finish, he soon began to struggle with injuries again, retiring after three rounds of the PGA Championship the following month. He then had to sit out the US Open altogether before missing the cut in emotional fashion at St. Andrews.
Following a long absence, Woods was set to play in the Hero World Challenge at the start of the month but withdrew due to developing plantar fasciitis in his right foot.
Montgomerie reckons Woods has very little chance of adding to his 82 wins on the PGA Tour at this stage in his career.
"I don't see him doing that. People will say, 'Oh, come on, Monty.' Listen, yes, he's great. But Tiger doesn't have to now just get back to the standard he was performing at then. He has to improve it.
"The standard is improving all the time, and there's not one or two guys that can beat him now. There's 22 guys that can beat him. So, it's Tiger trying to get not back to where he was but to get to a standard he's never been at before and I don't think that's possible. I can't see that happening. I'd love it to happen because it's great for the game. I would love him to win. But I just can't see it happening."