It is his hope that this time around the local wildlife at Cathkin Braes in Glasgow will be better behaved. That way the Dumfries-born rider can concentrate on the task at hand: successfully navigating the twisting, rock-strewn trails in his bid for a medal.
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Montgomerie is one of five cross-country mountain bikers, alongside Grant Ferguson, Kenta Gallagher, Lee Craigie and Jessica Roberts, named as part of Team Scotland's largest cycling squad for Glasgow 2014.
The 31-year-old has been a regular face on the mountain bike scene over the past two decades.
"I started when I was 10," he says. "I sort of fell into it when I went to Ae Forest near Dumfries and had a demo day on mountain bikes. I started racing as an under-12 and progressed right through."
His chosen discipline is certainly not one for the lily-livered. "You are racing at 80-90% of your max heart rate for the full hour-and-a-half," he says. "Plus, the terrain is rough. You feel it on a Monday morning for sure."
Cycling was first introduced to the Games in 1934 and has featured at every one since, but mountain biking is a more recent addition in 2002.
Already Montgomerie is sizing up potential rivals when it comes to Scotland's chances of a podium place. "Australia, New Zealand and Canada are the three big ones in the Commonwealth, but Scotland aren't far behind," he says. "I would say Scotland has one of the strongest teams with Grant, Kenta and myself."
Each, he says, brings a different style of riding to the team. "Both Kenta and myself are fast starters so we can put ourselves into the race from the beginning whereas Grant tends to come through [later]," says Montgomerie. "It's going to be interesting and I think we are all going to be up there in the mix, battling for medals."
It marks his third shot at Commonwealth Games glory. In Melbourne, Montgomerie was the highest-placed Scottish finisher, crossing the line 13th. When cross-country mountain biking failed to be included in Delhi four years later, he attempted to forge an alternative path.
"I switched to the road for a couple of years to try to qualify for the Games but that didn't come off," he says. "After Delhi I switched back to racing cross-country again with new focus and goals."
Montgomerie has already been hitting the trails around Cathkin Braes in a bid to maximise the potential home advantage come July 29. "I've done three races on the track already, plus a week-long training camp there a couple of weeks ago," he says.
It is his belief that Glasgow 2014 will help stoke the interest of a raft of new cycling fans. "The Games are going to bring it to TV and a wider audience," he says. "Whereas the focus has been on downhill for the last few years, I think this is going to rejuvenate cross-country mountain biking in Scotland."