Dundee will face an entirely new opposition in Welsh Premier League side The New Saints next month.
The Dark Blues were paired against them in the third round of the SPFL Trust Trophy.
Gary Bowyer’s side will travel to face TNS on the weekend of September 24 and 25.
According to stats site The Dee Archive, Dundee have never faced a Welsh side in their 129-year history.
Courier Sport takes a look at who they are and what the Dens Park side could come up against.
Who are The New Saints?
The New Saints play in the Welsh Premier League – and are the most successful club in the Welsh league system.
They play in green and white hoops and are managed by former Middlesbrough and Crystal Palace defender Craig Harrison, who is in charge for his second spell.
Last season, they were runaway champions, finishing 21 points clear ahead of nearest rivals Bala Town.
Not only did they romp their way to the league title but they made it a double by winning the Welsh Cup.
They beat Penybont 3-2 at the Cardiff City Stadium in May.
Their league victory gave them the opportunity to qualify for the Champions League, but they fell short in the first round of qualifying.
— The New Saints FC (@tnsfc) August 29, 2022
They lost out to Northern Irish side, and fellow Challenge Cup contenders, Linfield, 2-1 on aggregate.
They then had a second chance of European football in the Europa Conference League but again crashed out in the qualifiers. They lost 2-0 on aggregate to Víkingur Reykjavík.
TNS have been involved in European qualifiers for the last 23 years.
So far this campaign, they sit joint-top of the Welsh domestic table after two wins and a draw.
Play in Welsh league – but not in Wales
Dundee fans planning on travelling to see their side would be forgiven for thinking they’ll be off to Wales.
In fact, they are off to Shropshire, just on the English side of the border with Wales.
The New Saints were initially formed in the village of Llansantffraid-ym-Mechain before becoming Total Network Solutions in 1996.
Fast forward to 2003, they merged with Oswestry Town to become ‘The New Saints’ and have been based in England ever since.
In 2006, they played their first game at their 3000-capacity Park Hall stadium.
While TNS are new opposition, a few players should be familiar to the Dark Blues.
Former Aberdeen and Dunfermline striker Declan McManus now plies his trade with the side. He moved from East End Park to the Welsh Premier League in 2021, for a fee thought to be around £60k.
McManus has since scored 32 goals in 45 appearances.
The 28-year-old has netted three times against the Dark Blues in his career. Most notably, he bagged a late brace to stun Dundee as Dunfermline pulled themselves back from 3-0 down to earn a point in December 2020.
Former Hamilton Accies pair Jon Routledge and Daniel Redmond are also in the TNS squad.
Routledge has netted once against Dundee, equalising in a 2-2 draw for the Accies in the 2011/12 season.
Redmond meanwhile hasn’t scored against the Dee, but has assisted three goals in 10 appearances against the boys in dark blue.
What the managers said
After the draw was made, boss Craig Harrison, who helped TNS to the Challenge Cup semi-final in 2017 and Connah’s Quay Nomads to the final in 2019, said: “It will be a tough game – it softens the blow a little bit with it being a home tie.
“If it had been away, it would have been a really tough one against a Championship side and Dundee are a big club in Scotland historically.
“It will be a tough game but one everyone is looking forward to.
“Getting back in the Challenge Cup is something I have enjoyed, both at my time at TNS and Connah’s Quay.
“I’m looking forward to it and so are my players.”
Dundee boss Gary Bowyer said: “It’s my first experience of the competition. I bought a striker from TNS a few years ago, Scott Quigley, who is at Stockport now.
“It’s astroturf but it is what it is, we have to go play it and we want to win it.”