No club has escaped the Championship after failing to finish inside the top two since the SPFL introduced the current lopsided play-off system eight years ago following league reconstruction.
The only two clubs who have gone up via play-offs, Hamilton in 2014 and Livingston in 2018, finished runners-up and successfully made it through two two-legged ties, rather than the three that await the Fife derby rivals.
Raith boss John McGlynn who saw his side agonisingly pipped to second place by Dundee on the final day of the league season, is relishing the chance to rewrite the history books as he challenged his players to become club legends.
"It’s never been done before but I like that kind of challenge. It stacks up really well," he said. "If we look back in years to come and say ‘Raith were the first to do that’ that would be another tick of the box, something to be very proud of.
"That’s the challenge. Hopefully we can do it. We have that togetherness, that team spirit, allied to the way they play football. If we get that wee bit rub of the green in front of goal. You just never know."
In normal circumstances the match would be played in front of a 12,000 sell-out crowd, as was the case for the last promotion decider between the local adversaries at East End Park towards the end of the 2010-11 season.
The Pars won that clash, and secured promotion, but were relegated the following season and have not been back to the top table since, while Raith have to go back to 1996-97 for their last campaign among the big boys.
"It has been a long time since Raith have been in the top flight but that’s the ambition and desire we have," said McGlynn, who will have Iain Davidson available after the defender’s appeal hearing against his red card in Friday’s 4-0 defeat to Hearts was delayed until Wednesday due to the bank holiday.
“We have this opportunity as we have played well this season and we are there on merit.
“It would be massive to get to the Premiership. The carrot is there for Dunfermline and Dundee as well.
“They have been in the top flight more recently than ourselves so from our point of view, what an achievement this could be if we can do it.
“You talk about legendary status and it probably would be if we can get the club back there.
“We have been in League One and could we do back-to-back promotions to the Premiership, it would be dream come true stuff.”
The last two league meetings produced plenty goals and a share of bragging rights with a 4-1 home win for the Pars followed by a 5-1 Raith victory in March.
"I'm only looking forward. The three league games are gone," stressed Dunfermline boss Stevie Crawford. "We know what's at stake and we're very much focused on the game.
"I believe in my players. I want them to go out and express themselves and not have any fear.”