Gleeson shifted across the Pacific in early 2010, before the Timbers had even joined MLS, benefiting from the Kiwi connections of the club's general manager, former All White Gavin Wilkinson, but played just a handful of games for the first team between his arrival and the end of last year.
The Kiwi began the 2016 season as the understudy to Ghanaian keeper Adam Kwarasey, but was swiftly promoted when Kwarasey jammed a finger into the turf early in the Timbers' campaign and was ruled out for several weeks. He immediately impressed, earning MLS player of the week honours after a game against Toronto FC in early May where he made four crucial saves, but the big vote of confidence came on July 18, when Kwarasey was transferred out of the club, leaving Gleeson as their sole senior gloveman going forward.
PHOTOSPORT
Jake Gleeson made his All Whites debut off the bench against Australia in 2011.
"I've waited six years in Portland to get an opportunity like this, and when it comes along, you want to take it and make the most of it and get out there and prove that you haven't wasted all those years," said Gleeson from Nashville, where the All Whites are in camp ahead of Sunday's game.
"It was a good opportunity, and one that I had to take full advantage of, and with how I've been playing, it's been pretty decent."
But while things are all rosy now, there were plenty of moments over the past six years where Gleeson wondered if his chance would ever come.
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Stefan Marinovic is the incumbent All Whites goalkeeper.
"The life of a goalkeeper's very difficult in that respect, only one person can play and generally for the season that keeper plays a lot. You always sit and wonder - am I going to get a chance? Am I good enough to play? And you don't really know until you get out there and do it," he said.
"I've still got a very long way to go and a lot to work on and a lot to improve on, but there were definitely times where I thought maybe I'm not quite up to it or maybe I'm not going to get that chance, or maybe I have to move somewhere else to get that chance that I need. I'm really happy that it worked out in Portland, because I love living there, and I love the club and the community."
Playing regular first-team football has been the catalyst for Gleeson's return to national duty, just in time for a 13-month stretch that starts with this month's two high-profile friendlies and is followed by the business end of 2018 World Cup qualification as well as the Confederations Cup next June.
As he looks to add to his eight All Whites caps - the last of which came in November 2014 - Gleeson will have plenty of competition, but he says he doesn't mind that that's the case.
"With some of these guys coming through like Stef [Marinovic, the incumbent], who's obviously done a great job, and Max [Crocombe], who's over in England, they're good goalkeepers. Tama [Williams] is in here as well, and it's real competitive, and that's the environment that you want, you don't want to come in and not have a competitive environment, you want to be pushing each other."
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