If you glance at the fixtures for the third round of the Scottish Challenge Cup two immediately leap out: in Dublin Bohemian play the English side Sutton United while Northern Ireland’s Coleraine head to the Welsh town of Connah’s Quay, two matches in which the principal Scottish challenge will be to locate a Scotsman.

“It is a little bit odd, that an English team’s playing an Irish team in a Scottish cup,” says Derek Pender, the Bohemian captain, for whom victory – and a place in November’s quarter-finals – would bring an unusual challenge. “The competition, the way it’s set out, is a bit odd. We’ve only got two weeks left of the season and if we win on Saturday, I don’t know how it’s going to work. I think nearly every one of our squad is out of contract on the last day of the season – the club will want to keep most of the players and Keith [Long, the manager] is trying to get everyone tied down, but the majority of the squad have contracts that end in two weeks. So we’ll see what happens if we get through.”

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Whereas teams from Northern Ireland and Wales have been involved in the competition since 2016 and those from Republic of Ireland were admitted a year later, this is the first season in which English sides have been invited. The move has been unpopular in some quarters but according to Paul Doswell, Sutton’s manager, when they travelled to Airdrieonians in the second round they were greeted with open arms (and, as they eked out a 1-0 win, defences).

“It was fantastic,” Doswell says. “The chairman said it was one of the best welcomes he’s ever had in a boardroom, and the way we were looked after was first class. There were no problems because we were English whatsoever. A few of us watched England play Spain in the local pub, and that wasn’t an issue either. It was a good trip and we’re very, very excited about the trip at the weekend. As a club we very rarely have the opportunity to stay overnight somewhere and enjoy each other’s company. It’s a taste of something different.”

Connah’s Quay Nomads, managed by the former Manchester City captain Andy Morrison, won at Falkirk in round two but are not new to the competition, having also been involved last season. “I’ve not felt any negativity around it,” says Morrison. “I can’t speak for the Scottish clubs but for the rest of us it’s a fantastic opportunity to test ourselves against Scottish Championship teams and see where we are in comparison to them. I do understand that it is their cup, but if it’s their cup they need to go and beat the teams that are coming in. Our opponents have made us very, very welcome. It’s been great, and it’s a massive scalp for a Welsh part-time team, to beat a Scottish full-time team.”

Facebook Twitter Pinterest Connah’s Quay Nomads, in red, are the only Welsh team who have reached the third round of the Scottish Challenge Cup. Photograph: Gareth Iwan Jones/Guardian

The draw has been particularly harsh on Sutton, who are the only foreign side to play away twice. They have also been forced to move two potentially lucrative home league games from Saturdays to midweek. “When we were invited into the competition it was on the basis of getting £5,000 if you went to Scotland and £10,000 if you went to Ireland,” says Doswell. “It cost substantially more than that for us to travel up to Airdrie, which put us out of pocket, and this time we’re going to go just slightly over. For a club with limited means as we are, it’s something we’d definitely have a closer look at next time.

“We picked up a couple of injuries at Airdrie – one was the skipper, who’s massive for us and has been out for a month since then. We missed the game against Boreham Wood and subsequently lost it at home on the Tuesday, after we’d been away at Airdrie and they’d played at home to Dunfermline – I think that made a big difference on the night. Now we’ve lost Barnet at home on national non-league day, which would have been well over 2,000 people, and we’ll play them on a Tuesday night in November.

Nobody in Scotland has any idea about a small village in the north-west point of Wales. It is an unknown entity for them Andy Morrison

“I’m not negative: Airdrie was brilliant, the Dublin trip everyone’s looking forward to. We’d never played in Ireland or Scotland in a competitive match, so it’s history-making as well. There are plenty of positives, but the financial and injury sides can impact more than you think when you gleefully say yes in June or July.”

Tactical preparation for matches against unfamiliar and distant opponents on a tight budget represents another unfamiliar challenge. Bohemian sent someone to watch Sutton, but Doswell has had to make do with some recorded highlights. Morrison travelled to Coleraine to see them play Ballymena last month, though Eoin Bradley’s 16th-minute red card meant the trip was of limited use. “There’s a feeling of unknown in this competition,” Morrison says. “Nobody in Scotland has any idea about a small village in the north-west point of Wales; it is an unknown entity for them. Nobody knows what to expect from the Welsh league. I think Falkirk were very surprised at how good we were, and we came away with a great deal more credit and respect than we had before we showed up.”

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Inverness Caledonian Thistle beat Dumbarton in a satisfyingly Scottish conclusion to last season’s competition, but attitudes to the international entrants might be different had the two semi-finals gone the other way, which would have resulted in a Wales v Northern Ireland final. “My view is that the English clubs were invited to help spice up a competition that was perhaps going stale their end,” says Doswell. “I don’t think there were too many national newspaper articles written about it last year. It’s given the competition a different angle and it’s given the sponsors better coverage, but whether it’s going to work again I don’t know. From our perspective, given the chance again, would we have entered it? Probably not, if I’m being honest.”