But now the Rabs gaffer has turned his attention to perhaps an even more unlikely triumph - bringing a World Cup back to Scotland.
Maxwell is part of the Scotland squad which headed out to Thailand on Friday for the 12th World Seniors Cup.
It’s third time he has been involved in the competition which aims to raise money for victims of the tsunami which struck Asia in 2004.
Others in the Scotland squad include Stewart’s coach at Rob Roy, Kevin Finlayson, and current Kilsyth Rangers Alan Flanigan.
Former Partick Thistle and Dundee player, and ex-Cumbernauld United manager George Shaw is also in the squad, as is ex-Falkirk boss Gary Holt.
Scotland will compete against England, Iran, Thailand, Taiwan, Australia, New Zealand and the USA. Last year’s glory bid ended with a 3-1 semi-final at the hands of an England side which included the likes of former Everton star Peter Beagrie.
Stewart said: “There are three [age] categories - 38 to 43 young category, middle category 43 to 49 and over 49.
“The 11 on the park at any one time, the goalkeeper can be any age over 38, there’s got to be three young category, four middle and three old. In the young and the middle category when you’re off you’re off, the over 50s have rolling subs on and off so it’s slightly more technical than just a normal game of football.
“There are two groups of four with the top two going through to semi-finals and then the final; if you get there you play six games in seven days.”
With temperatures sometimes going up to 40 degrees it can be tough going, to say the least.
Stewart admitted: “Obviously the conditions don’t suit us Scottish guys but it’s a fantastic experience and ultimately it’s for a great cause.
“The Thai FA run it and all the money goes to the Tsunami fund for the kids. They move it around so that every year it goes to a different province, so every area benefits from it
“On our day off we do a coaching day and we take stuff over - kits, balls boots - and we give it out free to the kids.
“The guys fundraise their own money to get there so it’s not cheap, but we do it because it’s a good cause and we enjoy the trip.”
This year’s competition will be held in Phitsanulok, halfway between the northern city of Chiang Mai - where the competition was held last year - and the Thai capital Bangkok.
Given Scotland’s track record in recent season, perhaps one bonus is that Scots don’t have to qualify for the invitation-only competition. And while England and Iran will be the favourites, Stewart doesn’t rule out the chances of a Scotland suyccess.
He said: “The guys are looking forward to it, we’ve trained really hard, we’ll be prepared and with a wee bit of luck we’ll be trying to pull off a shock result.
“It’s a great experience, it’s a great trip and it’s raising money for a good cause. You get treated like royalty out there, everything is first class. “Hopefully we can put up a good show and you never know. We might just pull off the unthinkable and bring back a World Cup to Scotland.”