If they both progress to the semifinals, they will have taken vastly different routes.
Caversham could not have asked for a better draw. The South Dunedin club hosts Manukau City at the Caledonian tomorrow. On paper, the South Auckland club is the weakest side remaining in the cup.
It booked a surprise quarterfinal appearance by upsetting Papatoetoe in a penalty shootout.
While Caversham will start as a warm favourite, Dunedin Technical has a much harder road ahead. It will travel to Wellington to play the highly-fancied Miramar Rangers tomorrow.
It should be a fascinating battle but, on balance, the home side would have to start as the favourite, Dunedin Technical Mike Fridge said.
"I think Miramar is one of the top sides and not just in Wellington," he said.
"They've got a good pedigree and they are one of the top sides in the country, to be honest. They have a very good home record. I don't think they've lost a game at home this season.
"So I think they will be the favourites ... but we're going up with a lot of confidence as well."
Fridge is pleased with his side's preparation. Pressure has eased on the injury front, although David Hayman broke his collar bone last Saturday.
Nick Meglinski is with the Otago Milk Cup team in Northern Ireland, but Dunedin Technical is otherwise at full strength.
A couple of the faces in the Miramar line-up will be familiar.
Campbell Parkin played for Dunedin Technical and Patrick Fleming played for Caversham.
While Fridge has been busy encouraging his side to believe this week, Caversham coach Richard Murray has had to approach the build-up from the opposite angle.
He has been on guard, making sure complacency does not sneak into the camp.
"If you looked at the players on paper you could quite easily slip into a relaxed mode and think it is going to be a walk in the park," Murray said.
"But cup football loves the underdog. If we go in complacent, we will be in a lot of trouble. Our goal for the season has been to play better each week and that is the same this week. We've got to build on the confidence we've got from the last month when we've had good victories and really go hard at them."
Caversham has been strengthened by the return of Seamus Ryder and Anton Ross. Ryder will "bring plenty of experience and a lot football intelligence" and "Ross is a similar type of player".
Goal keeper Liam Little was a key figure in Caversham's 4-2 win against Cashmere Technical in the fourth round match and striker Tom Jackson's ability to find the back of the net is a real asset for the home side.
Dunedin teams in action
Chatham Cup quarterfinals
CAVERSHAM v MANUKAU CITY
Caledonian, tomorrow 2pm
Caversham squad: Liam Little, Craig Ferguson, Simon Ward, Benjudah Fitzpatrick, Michael Smith, Andrew Ridden, Seamus Ryder, Matt Bruin, Ant Hancock, Anton Ross, William Smith, Callum Flaws, Evan Jones, Tom Merrilees, Tim Cook, Tom Jackson, Harley Rodeka (c), Tim Horner.
Coach: Richard Murray
DUNEDIN TECHNICAL v MIRAMAR RANGERS
David Farrington Park, Wellington, tomorrow 2pm
Dunedin Technical squad: Michael Walker, Tristan Prattley, Matt Joy, Justin Flaws, Michael Flaws, Richard Smith, Victor Da Costa, Alistair Rickerby, Aaron Burgess, Tim Stokes, Liam Lockhart, Tim McLennan, Brad Rodden, George Milne, Tony Boomer.
Coach: Mike Fridge
