Last season there was a 2-0 win to each, and a 0-0 draw, as both teams struggled at the foot of the competition, and Canterbury eventually earned the wooden spoon in last position.
But Otago hope springs eternal, and supporters are keen to see United's new attacking team shape, in which Dave Dugdale stood out enough last week to earn recognition in the NZFC team of the week.
A key element in Caversham's winter success of winning the South Island Championship, Dugdale - a nephew of former All White coach Ken Dugdale - has fitted in seamlessly at United.
A good receiver of the ball, he has a real striker's talent for losing defenders after he unloads to team-mates such as Aaron Burgess, Blair Scoullar and last week's substitute, Tom Jackson.
Scoullar is out injured this week, so no doubt Jackson and Sean Brand will have been bursting balls at training to earn a place among Otago's starting side.
Diehard Otago United fans might have some difficulty recognising their team at Sunnyvale.
Of the squad that last played Canterbury United, and lost 2-0 in round 16 in March, only three players remain: Burgess, Andy Coburn and Mike Smith.
Gone are Nick Tarrant, John Dale, Kevin Taylor, Terry Alvino, Croyden Wheeler, John Lange, Jesse Malloy, Mike Eisenhut, Ben Keat, Mike Flaws and Chad Severs.
It is quite a turnover, fully justifying coach Terry Phelan's complaint that there is little continuity at United.
"We really have to build a new team from scratch each year," he said.
"But I have a good feeling about this year's squad. There is a balance of experience and youth that we have not had before, and I think we have a real chance of making the top four.
"Last week we played the ball around well against Auckland, and they are a top outfit. We also made goal-scoring chances, and with an ounce of luck should have had a couple of goals.
"Considering it was virtually our first proper match, I was pleased with some of the combinations, and I am sure we can build on that performance."
However, having been involved in more than a few derby matches in the English premier league, Phelan realises there will be an extra element of competition in the match with Canterbury.
"There will be passion, as there should be, but we want to show discipline and control, keeping our team shape and not giving the ball away cheaply."
Canterbury coach Koroush Monsef finished last season well after taking over from former coach Danny Halligan in the 10th round, and looks to improve after strengthening his squad this season.
A key signing, yet to be confirmed, is former Waitakere and Solomon Islands international striker Commins Menapi, who could sharpen Canterbury's attack, especially working in tandem with countryman Michael Fifii.
Influential Scots midfielder Stu Kelly has not been passed fit and his place is likely to be taken by Hamish Chan, but Monsef is sure his side is capable of earning its first win.
Otago v Canterbury
Sunnyvale, tomorrow, 3pm
• Otago United: Liam Little, Rhys Henderson, Tristan Prattley, Barry Gardiner, Colin Falvey (captain), Michael Smith, Robbie Deeley, Morgan Day, Tom Jackson, David Dugdale, Andy Coburn, Aaron Burgess, Callum Flaws, Sean Brand, Tim Horner.
• Canterbury United: Adam Highfield, Matt Boyd, Bill Robertson, Andy Pitman, Ryan Faichnie, Garry McDermott, Tom Lancaster, Jamie Smith, Gareth Turnbull, Michael Fifii, James Reichwein, Nick Wortelboer, Darren Overton, Hamish Chang, Ben Harris, Chris Sinclair.
