In 1990, when Howard Wilkinson's team escaped the old Second Division thanks to a final-day winner from Lee Chapman amid chaotic scenes at Bournemouth, Grayson was a 20-year-old reserve defender waiting by his transistor at home in Yorkshire. The news from the south coast impacted on him personally and professionally.
"I had a new house riding on it," the current Leeds manager, now 40, recalled on emerging, drenched in champagne by his jubilant players, after they beat Bristol Rovers on Saturday to seal their ascent from the third tier. "I was listening to the radio, praying we went up because it would be worth a bonus. I was desperate for us to go up as it meant an increase in my wages. My house was safe after that."
Leeds' return to the Championship should have been as safe as houses after they amassed 56 points in the first half of the campaign. Yet they had gleaned only 27 from the second half prior to this finale, piling pressure on Grayson as he pointed, cajoled and screamed from the touchline. This time, more than bricks and mortar were at stake.
Failure to win might have consigned the 2001 Champions League semi-finalists to an unthinkable fourth season in the lower half of the League. With that would have come drastically reduced season-ticket sales and the almost certain departure of Leeds' most prized assets, plus the inevitable speculation over whether Grayson was the man to take them forward.
When it was all over, Jermaine Beckford having followed Chapman into Leeds folklore with the winning goal after Leeds shrugged off the setbacks of being reduced to 10 men and falling behind in the second half, Grayson immediately set his sights on regaining the Premier League status they surrendered in 2004.
"I think getting out of League One for Leeds United was harder than getting out of the Championship will be," he said. "We're a big scalp in this division. I know the Championship is a difficult league and there are some really big teams in there, but it doesn't frighten me."
During Leeds' FA Cup run, which saw them win at Manchester United and draw at Spurs, Grayson spoke, from the position as runaway leaders of League One, about going straight through the Championship. Their subsequent decline in form and results made such talk sound fanciful, prompting him to accuse certain players of "believing their own hype".
So there was now an understandable wariness of making rash declarations that might be seen as hostages to fortune. "I won't say 'We will be promoted next year'," Grayson said. "But I am an ambitious manager and I want to get this club in the Premier League. Not being the biggest scalp will help us. It's a challenge we'll embrace."
The club Leeds prised him from 18 months ago, Blackpool, are currently vying for a place in the top flight. However, it is another of the Championship play-off contenders – a club he joined for £50,000 in 1992 – whose progress after climbing out of League One he seeks to emulate.
"Leicester City are a decent role model to follow. I firmly believe Leeds are a bigger club but I don't think they're a bad example. I am not setting any targets. But every time I kick off a season with a club, I want to get promoted, regardless of what division I'm in. That will be no different next season."
Exactly what sort of transfer kitty Grayson can expect from Ken Bates remains to be seen. Despite an average crowd of 25,000, some 3,000 above their reported break-even figure, and the £6m-plus received from Aston Villa for Fabian Delph, Leeds have invested modestly in players since the summer of 2007 when it looked as if the descent into receivership might be the end of the club.
Since then, the question of who actually owns United has become shrouded in mystery. The majority shareholding is held by Forward Sports Fund, a company registered in the Caribbean island of Nevis. Bates, though, continues to be its public face, and he insists Leeds are "trading profitably" with their financial crisis "now behind us".
"The chairman is as delighted as me that we've won promotion," Grayson said, "but conversations about money can wait for early next week. We'll have a good couple of days and he has organised a trip for the players and staff. Now that it's in the press, we can hold him to that promise. We are not sure where we are going – Filey or Bridlington, probably!"
Saturday evening, barely an hour after the pitch was cleared of thousands of delirious, almost disbelieving fans, was not a judicious moment for Grayson to begin publicly evaluating his squad. But Leeds' results and performances since the extraordinary January day at Old Trafford must have made him aware of the need for greater quality; they won only one game out of 10 against members of the top six, and that was a fortuitous victory over Norwich.
He has already been linked with the Scunthorpe striker Gary Hooper and the Sheffield United trio of Billy Sharp, Nick Montgomery and Chris Morgan. Sharp, who has scored freely on loan to Doncaster, and Hooper are the kind of proven finishers Leeds will need if they lose the out-of-contract Beckford.
"The results from the first half of the season showed what a good group of players we have," Grayson said, although Leeds lost nine of the last 23 matches after only one defeat in the first 23. "I genuinely believe a large number of these lads can cope with the Championship but we will need to strengthen. We have to move forward. I brought players in last summer to get us promoted. I'll give them the opportunity to take us forward but I also have to be ruthless because I want this club to be successful. Every step up has to be with an improvement. We'll need new players and I'll do that."
The old players are always in evidence at Elland Road, with Eddie Gray, Norman Hunter and Mick Jones joined on Saturday by John McClelland and Brendan Ormsby from later eras. The trio from Don Revie's famous/infamous team know all about snatching anguish from the jaws of euphoria, yet even by their standards Leeds made hard work of it.
"Maybe it was destiny that we would go to the last game," said the one-time apprentice known as "Larry", who grew up steeped in the feats and frustrations of Gray and co. "It's been a long season for everyone connected with the club. The players will disappear next week for seven weeks and I'll get a holiday at some stage. But come Monday and Tuesday, I'll be planning for next year."
And, it seems, for the one after that, possibly in the Premier League. "We want to get back as soon as possible," Grayson said, his hair matted with bubbly. "There are no unrealistic targets, but we'll give it our best shot."
Leeds' turbulent decade
By James Mariner
*May 2001: Lose 3-0 to Valencia in the Champions League semi-finals.
*June 2002: David O'Leary sacked after failing to reach Champions League.
*March 2003: Peter Ridsdale resigns as chairman with club's debt over £119m.
*May 2004: Defeat at Bolton confirms relegation from the Premiership.
*January 2005: Ken Bates takes over as chairman at Elland Road.
*May 2006: Lose 3-0 to Watford in the Championship play-off final at Cardiff.
*May 2007: Relegated from Championship after entering administration.
*May 2008: Reach play-off final despite 15 point deduction, but lose to Doncaster.
*December 2008: Simon Grayson succeeds Gary McAllister as manager.
*May 2009: Lose 2-1 on aggregate to Millwall in League 1 play-off semi-finals.
*January 2010: Jermaine Beckford secures 1-0 FA Cup third-round victory at Manchester United.
*May 2010: Promoted to Championship after three-year hiatus.
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