Ryan Gauld v Barry Smith: The alternative Dundee derby taking place in Canada

Former Dundee boss Barry Smith was last in Scotland with Dumbarton.

Nestled nicely between the end of the last international window and before the women’s Euro 2022 tournament gets under way next week is the Canadian Championship semi-final between Vancouver Whitecaps and York United, which kicks off in the early hours of tomorrow morning.

Better still, the meeting contains local interest. Local to Scotland that is. A Scot is guaranteed to reach the final though whether it is Ryan Gauld, playmaker with the favourites Vancouver Whitecaps, or Barry Smith, assistant manager of York United, remains to be seen.

The smart dollars will be on Gauld, who it was recently revealed earns US$2.265 million a year. The York United budget is around CAD700,000 in total.

Former Dundee United midfielder Ryan Gauld had a brief spell on loan at Hibs in 2019.

The clash between one of Canada’s three MLS representatives and the team currently lying sixth in the eight-team Canadian Premier League has been portrayed as a David v Goliath contest. Smith knows all about winning out against long odds.

He was manager when Alloa Athletic reached the final of the Petrofac cup after a stunning comeback win over Rangers in 2014. Smith also steered Dundee to survival in their so-called "Dee-fiant" season in the Championship when they were hit by a 25-point penalty following a second spell in administration.

Now 48, Smith, whose last position in Scottish football was as an assistant to Jim Duffy at Dumbarton, felt the need to head elsewhere to reboot his career. He feared his past achievements risked being forgotten about in the rush to hire younger coaches.

“The defiant thing was great and something I am proud of,” he says. “But they forget when you go to Alloa and what an achievement it was keeping them in the Championship and getting to a cup final. And East Fife, from second bottom in the league to within a point of the playoffs. I think I proved myself.”

No stranger to adventure having spent two seasons at Valur in Iceland, he has gone to even greater lengths this time by making it all the way across the Atlantic to join York United, a club formed in 2018. They are now run by Dundee-supporting CEO/President Angus McNab.

That quirk alone did not guarantee Smith the job, although it can’t have harmed his chances. He also found manager Martin Nash’s views about football tallied with his own. “You know the way Scottish football works,” says Smith. “Over here they are not averse to hiring someone they don’t know. He recognised I know my football, which is there for everyone to see.”

You don’t stand joint third in a club’s all-time appearance list – in this case Dundee – without knowing something about the game. But he has encountered some new challenges since arriving in snowbound Toronto in February. When he speaks to The Scotsman, he has just disembarked from the near five-hour flight to Vancouver.

“The traveling is obviously different, it is quite intense” he says. “You are on the road quite a lot but you can’t do anything about that. Canada is a massive country.”

Vancouver Whitecaps represent the biggest test – to date. Toronto FC take on MLS Eastern Conference rivals Montreal in the other semi-final. The winners of Canada’s only domestic cup competition for professional teams gain automatic entry to the CONCACAF Champions League.

For Smith, it is a first meeting with Gauld, who was just breaking into the Dundee United side when he left Dundee during an ill-fated top-flight season in 2012-13.

“I know Stevie Campbell, who coached him and raves about him. It’s strange that this is how – and where – we should meet.”