Doncaster boss Sean O'Driscoll and Leeds manager Gary McAllister
In 2001, Leeds reached the semi-finals of the Champions League and secured a top four place in the Premier League for the third year running. Doncaster finished ninth in the Conference.
Yet on Sunday they will meet on equal terms in the League One play-off final at Wembley, with a place in the Championship at stake.
"It's not something Doncaster would have dreamed about," said Ian Snodin, who captained both clubs during the 1980s before going on to win a League Championship medal with Everton.
"Donny have come a hell of a long way in the last 10 years from when I was manager in the Conference.
"When I first took over we had no nets, no kit and no balls and now they are one step away from the Championship.
"The chairman said 10 years ago that he would retire when he had his ambition of Doncaster playing Championship football because he always believed a town like Doncaster could handle a Championship team.
"But I doubt now that he will retire if his dream comes true. He will want to continue," Snodin told BBC Sport.
Despite being born along the road in Rotherham, Snodin became a Doncaster hero, playing over 200 games and earning his first England under-21 caps while they were playing in the old Third Division under Billy Bremner.
When he ended his League career with Scarborough, Snodin was the man Doncaster turned to after their own Football League days were temporarily ended by relegation in 1998.
O'Driscoll has already proved his worth to Doncaster
Just as importantly, in the aftermath of the Ken Richardson era - which ended with the club's former owner in jail following a bungled arson attempt at their old Belle Vue home - local millionaire businessman John Ryan also took a hand in restoring the club's credibility.
With Ryan's substantial backing, Snodin steadied the ship, then Dave Penney delivered back-to-back promotions to take Rovers into League One by 2004.
Their return to the second tier of English football for the first time in half a century was followed up by a move to an impressive new ground, the Keepmoat Stadium, last year.
"Now they have a stadium which is second to none and a great little footballing side - it's tremendous for the whole town," said Snodin.
"And it's great for me personally to have two sides who I captained being in a Wembley final.
"I loved my time at Leeds and I would love to see them back in the top flight, not just the Championship.
"But I started at Donny as a 14-year-old, played for and managed them and my heart is with them. But I see it as a great opportunity for both clubs."
For Leeds, it is a chance to reverse the downward spiral of financial meltdown, relegation to League One for the first time ever, and a 15-point penalty for infringing League rules on exiting administration.
I don't think there's anything between them. Doncaster were the better team in both league games but Leeds looked strong against Carlisle.
Ian Snodin
"In my eyes Leeds are a Premier League team with a Premier League ground but it's been a traumatic couple of seasons for them," said Snodin.
"They'll sell out their tickets in a day or two, that's how big they are."
Throughout their troubles, Leeds' fan-base has remained loyal with the home leg of their play-off semi-final against Carlisle attracting a gate of over 36,000.
And it is another former playing favourite who got them over the finishing line and into the play-offs, with the help of inspired loan signing Dougie Freedman and local lad Jonathan Howson.
"Dennis Wise did a reasonable job as manager against all odds because the fans were dead against it from day one because of his Chelsea connections," said Snodin, whose brother Glynn also played for both Leeds and Doncaster.
McAllister was part of Leeds' glory years in the early 90s
"They got to warm to him but when he left Gary McAllister, a former Leeds player, came in and he loves to play football the right way.
"He was a great player and has started to instil that in Leeds."
No team at this level is more stylish than Doncaster, however, with the quietly spoken Sean O'Driscoll having a big impact since taking charge in the early part of last season.
"The Doncaster fans were asking "Sean who?" when he got the job," admitted Snodin.
"He took some warming to, because he's not the type to go shouting and bawling but the football they have been playing, especially when they beat Southend 5-1 in the semi-final second leg, has been the best in the division, and better than some in the Championship.
"That's the way Sean likes to play. I don't know if they will be out-battled by Leeds and they will have to match Leeds in all departments but it should be a decent football game."
So with promotion and Yorkshire pride at stake, who will prevail?
"I don't think there's anything between them," said Snodin.
"Doncaster were the better team in both league games but Leeds looked strong against Carlisle.
"When you were a kid these were the games you dreamed about playing in so it's about who doesn't freeze, who settles down and takes the game by the scruff of the neck."
Bookmark with:
What are these?