The North End boss has promotions with Blackpool, Leeds and Huddersfield on his CV and would complete a quadruple should he mastermind his current club's ascent into the second tier.
However, even with Preston in the midst of a 12-game unbeaten run in the league, their aspirations of acquiring an automatic promotion berth are fading fast with second-placed Brentford seven points ahead and with two games in hand.
Grayson acknowledges that the form of leaders Wolves, Brentford - who went on a 19-game unbeaten streak midway through the campaign - and early pace-setters Leyton Orient has left Preston with a severe mountain to climb.
"Any other season, you look at the points tally and you wouldn't need half as many points," he said.
"It's been a very high standard from the teams up there, full credit to them. We'll just keep going and if we can win nine out of nine we still might have a chance."
The play-offs would hold no fear for Grayson given his habit of elevating teams out of this division, but he wants the Lilywhites to pursue a top-two spot in case any of the three sides above them falter over the finish line.
He added: "There's nine games to go and we want to win as many games as possible; we'll be kicking ourselves if we slacked off and teams start dropping points.
"We'll go all-out to win every game, as we have done all season, and if we can't catch the top two you say well done to them - whoever they may be - and then we go into the play-offs.
"We're confident if we go into that because we've got a good group here and if they don't manage to see it through we'll go into the play-offs full of confidence that we can go and get promoted that way."
- Sports & Recreation