The winners of the tie - which begins on Wednesday night at Central Park - will earn lucrative rewards from games against Rangers, Hearts and perhaps even Hibernian next season. The cost of defeat is higher still.
"This may be the biggest ever Fife derby between the two clubs," said the Cowdenbeath manager. "The future of Cowdenbeath lies in the hands of those players over the next two games.
"If I was one of them I know what my motivation would be. The thought of anyone from Dunfermline running out at Ibrox or Tynecastle next season would absolutely kill me and I'd want to make sure that doesn't happen. If we play to our best we can beat anyone and I know we're good enough to get past Dunfermline."
The Fife side were certainly good enough to ease past Ayr United on Saturday. Goals from top scorer Kane Hemmings, Greg Stewart and Tom O'Brien gave the home side the win on aggregate, despite a riposte from Michael Donald. He scored before half-time.
Ayr are consigned to another season in League 1 and Mark Roberts will lead the way as manager after signing a new one-year contract. It was not an announcement greeted warmly by all of the part-time club's supporters.
"The fans can shout all they like but it doesn't bother me," he said. "I've been in the game for a long time and I'm not going to cry about it. They've got their opinion but I don't agree with them. I believe I've done well here."