One of them is certain to taste that disappointment again, perhaps both.
The Highlanders have nailed the Chiefs 36-9 and 20-17 this season but a third success, even under the roof in Dunedin, looks lineball at best. Here's why:
The Chiefs' scrum claimed two penalty tries in their opening game, the Charlie Ngatai/Sonny Bill Williams combo gives them stronger midfield heat, Brodie Retallick is back and Sam Cane comes off his rest.
Issues to sort are first five-eighths and whether Hika Elliot is fit for his 100th game.
The Highlanders need both Malakai Fekitoa and Nasi Manu to recover from their injuries to add another layer of cement to their resilient combinations.
Having another fit lock is an issue and if Waisake Naholo's damaged arm is still giving him gip, there goes one massive line of potency.
However, the Highlanders have played under all sorts of pressure throughout the season and lost only five matches - twice to the Canes, the Crusaders, Brumbies and Lions.
They have three All Blacks who are stars of the game and adhered to the national selectors' demands to rest while their teammates are unheralded locals, discards and imports who work overtime to make the most of their ability.
Nail on the growing coaching sense of Jamie Joseph, Tony Brown and Scott McLeod who tap into all the underdog sentiment and that creates a powerful combination.
Statistics dominate the modern coaching world but no one can measure passion, mood, grit and heart and it's these parts which are such wealth in rugby - players who get up to make another tackle, hit a ruck or run a decoy support line.
Not many outside immediate family and the Highlanders' fan club will be able to name their latest tight five selection but they got the latest job done and set the scene for those to follow in Saturday's sudden-death.
The bulk of expectation will sit with the Chiefs - twin champions, the poster-boys for selection smarts who have such an innovative and hard-edged coaching group.
They lost last year's playoff to the Brumbies in Canberra, now they are away once more facing a similar obstacle. Two falls against the same foe are two looks at how to come up with a solution.