Greatholder said it'll be an eye-opening experience for his players who've excelled at their current level having conceded only six goals in their opening seven matches.
"There'll be a reality check with how quickly you need to make decisions, how quickly the ball moves, how quickly you have to move into space and react to things at that level of football," he said.
While not expecting to progress to the next round of the prestigious knockout cup competition, the coach said he'll find a way to fit the next round of the Chatham Cup into their already tight schedule if needed.
"Bring it on if we do happen to get a result down there," he said.
"That won't knock us off track for what we're trying to achieve in the league this season at all – especially with the size of our squad."
Away from the cup, Greatholder said his team have made some big strides in the Central Federation League as they aim to keep their winning streak going.
The Wanderers' side started the season with a big list of injuries, with seven players unable to play their first few matches.
"Everyone needed to dig deep, it was a case of getting through the first few weeks with results," he said.
"And since then, we've built, the players have come together in a really strong way. You can't always get the culture right, but this feels really good at the moment."
The Havelock North coach said there will be quite a few fans travelling to watch the cup game at David Farrington Park in Wellington at 2pm on Monday.
"If we get our goals this year and we do get in the Central League then it's your bread and butter that travel for next season," he added.
