Mosgiel, Caversham and Otago University all make the trip to Christchurch for third-round matches.
It will be the first trip away for each, after having either played at home or against each other.
For Mosgiel, it doubles as its first encounter with a Mainland team.
It plays Coastal Spirit at 12.30pm tomorrow at English Park, looking to follow up last week's 3-1 win over University.
While it will be its first trip away, the travel factor is not entirely new to the Mosgiel players. Many of them have played for Southern United in the national league which can have tough travel arrangements.
"Luckily, most of the players have dealt with it with national league - either youth or senior national league," coach Cam McPhail said.
"But it's certainly something we're aware of.
"[So we are] making sure we get enough sleep, hydrating, making sure we're eating the right food - especially travelling up; we're going to find some decent food for the lads.
"So it comes with its challenges, but you've got to accept it.
"You can't make it an excuse for a poor performance. You've got to get on with it."
He added that for players with higher aspirations it was something they had to get used to.
After going unbeaten through the local league, Mosgiel had a hitch in a loss against Caversham first up in the South Island league.
That came after a lengthy break and McPhail felt the team had looked a little rusty.
It was back to its best last weekend in a 3-1 win over University.
Two late goals proved key. Riley Anderton helped Mosgiel into the lead seven minutes from the end.
From there, Lewis Wall scored his second of the game in injury time.
McPhail said the game had been a must-win.
It comes up against a big, physical Coastal side which beat Caversham 2-1 last weekend.
Sticking to its own game plan would be key, as that was when McPhail felt Mosgiel played at its best.
He said the players were excited about their first game against a Christchurch side.
"Once we qualified for the league it's what we've been looking forward to - to get an indication of where you're really at.
"It's one thing to say you're one of the top teams in Dunedin.
"But whether we can come out of it and say we're one of the top teams in the South Island, that's where we're really looking to test ourselves."
Caversham plays Western at Walter Park, while University travels to Tulett Park to play Nomads.
Cashmere Technical hosts Nelson Suburbs in the other game.
All games kick off at 12.30pm tomorrow.
