Martin Foyle twice took City to Wembley during his spell as manager During his time as York City boss, Martin Foyle was living out of a local B&B for six nights a week.
In contrast, now in their seventh season in the Conference, City's place in Non League's top tier is beginning to look more than simply a temporary residence.
Of course, it could have been very different. Foyle's men were surprise qualifiers for the play offs last term having flirted with the drop 12 months earlier when the ex-Port Vale boss took charge.
However, the 47-year-old engineered a turnaround in fortunes and, after seeing off Luton in the semi finals, they faced Oxford at Wembley for a chance to regain their place among England's elite.
It wasn't to be on the day, with Chris Wilder's side emerging 3-1 victors. It was the closest City had come to getting back into the League though.
They had also qualified for the play offs in 2007, but on that occasion lost out in the semis to Morecambe.
Having had to wait three years after that Morecambe loss to have another go in the play offs, City fans will now be concerned how long they will have to go until they get another opportunity.
Indeed, a look back into the history books makes depressing reading for the Bootham Crescent faithful.
Automatic relegation from the Football League was introduced in 1987, with one side taking the plunge into the Conference before being extended to two in 2003.
Ten different clubs were relegated in those 16 years, and two others - Maidstone and Aldershot - lost their place due to financial problems.
However, of those ten, Lincoln, Darlington, and Colchester all made swift returns to the League.
Halifax returned only to go down again and then out of existence altogether. Scarborough and Newport were not as fortunate - both clubs ultimately folding and phoenix clubs being established in their place.
Chester were relegated in 2000, returned in 2004 but, after relegation in 2009, then went out of business last season.
The other three - Barnet, Doncaster and Hereford have all since returned after spells of four, five, and nine years respectively, and remain in the 92 club today.
Of those sides relegated since two-up two-down was introduced in 2003, long-standing Football League clubs Shrewsbury, Exeter, Carlisle, Oxford, and Torquay all bounced back.
Kidderminster, Rushden, and Boston - promoted in successive years at the turn of the Millennium - all spent five years in the League before dropping back down to more familiar territory.
That leaves Cambridge United - relegated in 2005 - as the only other traditional League club besides York to currently be enduring a prolonged spell in the Conference.
The U's couldn't have come much closer though, and were beaten play-off finalists in both 2008 and 2009.
Like their League days, York's Bootham Crescent is a thing of the pastHowever, like City, they too have fluctuated between campaigns of challenging in and around the top five and struggling towards the bottom and fighting relegation.
The key, it appears, is getting out as quickly as possible. The longer you stay down, the harder it becomes to escape.
The problem for both is the longer they spend in the Conference the more the question must be considered: are they actually that out of their place?
After all, despite being the county town, when it comes to the footballing hotbed of Yorkshire, the Minstermen are very much the poor relations.
City will never be able to compete against the two Sheffield giants or Leeds. They will also always play second fiddle to the mining towns of Barnsley, Doncaster, and Rotherham, not to mention a resurgent Huddersfield.
Of course, it's not these clubs who York must try to compete against on the pitch. Instead, it is the wave of new Football League clubs who have made the breakthrough in the last decade.
The likes of Burton, Morecambe, Stevenage, and Dagenham may not have the pedigree of City, but they appear to be upwardly mobile clubs with an eye on the future.
It is reflected in the fact that three of them now play in purpose built stadiums, and the Daggers have been steadily re-developing their Victoria Road ground to coincide with their transition into the League.
A quick look around Bootham Crescent however and, for all its traditional lower league charm, it very much has the look of a past era.
While others clubs have been moving forward, the likes of York - who endured huge financial troubles in 2002 - have been standing still. It's no surprise they have been overtaken therefore.
It's no surprise either then that Minstermen supporters are now pressing hard for the construction of a new community stadium that the club can use. They know, as with many other clubs, it is crucial to their future.
Indeed, it shapes the entire question of where they wish their future to be. Without realising it, York are quickly becoming part of the Conference furniture.
Not only are they facing competition for promotion from an increasing number of former Football League outfits like Grimsby, Mansfield, and Wrexham, but also from wealthy upstarts like Fleetwood and Crawley.
It was a sign of the times that City were unable to hold onto their prized asset - striker Richard Brodie - when the latter came calling with a six figure bid during the summer.
Replacing Brodie, whose goals fired them to the brink of promotion last term, was never going to be an easy task. His loss, coupled with City's slow start this term, probably made Foyle's mind up that he could take the club no further.
The Brodie transfer was a worrying sign, too. In the past, City only lost striker Andy Bishop to a Football League club in Bury and they were able to reject a bid of £200,000 for fellow hitman Clayton Donaldson before he left on a free to Hibernian.
Selling Brodie to a Conference rival - and a smaller, if richer, club at that - would have stuck in the throats of York fans. If they can't compete with Crawley, can they compete at all?
Is the harsh reality that, despite once, during the '70s, spending a couple of years in the second tier of English football, York have now found a more natural level? Is simply returning to the Football League now the height of their ambition?
Just as their surroundings in an historic city hark back to a different era, are the Minstermen themselves going to be consigned to simply being part of the Football League past?
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