On Sunday, Scotland face Gibraltar 18 years to the day since they last secured qualification for a major tournament.
Whether they can still make the Euro 2016 play-offs by that time hinges on Thursday's Group D showdown against Poland at Hampden.
Fourth-placed Scotland are unable to achieve one of the two automatic qualification spots but a win over the Poles - who are in second - keeps a possible route to the finals in France open: a two-legged play-off against another third-placed team.
Three points on Thursday would mean Scotland could still catch Poland or the Republic of Ireland, as long as Martin O'Neill's side do not beat world champions Germany on the same evening.
The Republic travel to Poland for their final match on Sunday, while Scotland take on Gibraltar in Faro.
If both earn victories on Thursday, Scotland would need to beat Gibraltar and hope the Republic then win in Warsaw - that would see Gordon Strachan's side leapfrog the Poles courtesy of their better head-to-head record.
A draw against Poland would leave Scotland relying on Germany to take three points from Dublin.
It is not the first time Scotland have gone into a home match with the stakes so high. Here are seven previous occasions when qualification was on the line.
Scotland 2-1 Czechoslovakia, 26 September 1973
Willie Ormond's side had the 1974 World Cup in West Germany in their sights as almost 100,000 fans descended on the old Hampden slopes knowing a win would secure top spot in the group.
Zdenek Nehoda's shot slipped through the hands of goalkeeper Ally Hunter, stunning the Tartan Army into silence.
However, it did not stay quiet for long. Goalkeeper Ivo Viktor raced from his line as a corner came in, but he got nowhere near the leap of Jim Holton who headed Scotland level.
Then in the second half, after Billy Bremner had hit the post, the ball was lobbed back into the box for Joe Jordan to fire the hosts in front.
Scotland went on to become the first team at a World Cup to remain undefeated but not lift the trophy, after draws with Brazil and Yugoslavia and a win over Zaire.
Scotland team: Hunter, Jardine, McGrain, Bremner, Holton, Connelly, Morgan, Hay, Law, Dalglish (Jordan 64), Hutchison.
Scotland 2-0 Latvia, 11 October 1997
With Austria and Sweden going toe-to-toe with Craig Brown's side for a place at France 98 there was little margin for error. All three went into the final day of the campaign vying for two automatic qualifying spots.
As Hampden was being redeveloped, the games were shared around the country with Ibrox, Celtic Park, Rugby Park and Pittodrie all hosting the home qualifiers. Hibernian's Easter Road was set to be the next stop, but it soon became apparent the demand for tickets would be huge and it was switched across the M8 to Glasgow's Celtic Park.
Kevin Gallacher got Scotland on their way when he headed in after a John Collins shot was parried.
Gordon Durie sealed it when Gallacher's lob hit the bar and landed kindly for the Rangers striker to cement second place in the group and a spot at the finals.
Scotland opened the tournament with a narrow defeat by Brazil, before drawing with Norway and losing to Morocco, their last action at a major tournament.
Scotland team: Leighton, Burley, (B.McKinlay 89), Boyd (T.McKinlay 81), Calderwood, Hendry, Dailly, Gallacher, Lambert, Durie (Donnelly 84), McAllister, Collins.
Scotland 0-2 England, 13 November 1999
After finishing second in their Euro 2000 qualifying group behind the Czech Republic, Scotland faced a 'Battle of Britain' over two legs against the Auld Enemy.
Paul Scholes did the damage with two goals, first chesting Sol Campbell's cross down and firing past goalkeeper Neil Sullivan, then getting his head to David Beckham's free-kick.
Scotland had chances themselves. Kevin Gallacher fired straight at goalkeeper David Seaman when through on goal and Billy Dodds saw a lob come back off the crossbar.
However, it left Craig Brown's side with a mountain to climb in the second leg and despite a valiant effort that saw them win 1-0 at Wembley through Don Hutchison's header, it was not enough.
Scotland team: Sullivan, Weir, Dailly, Ritchie, Hendry, Ferguson, Dodds, Burley, Gallacher (Burchill 82), Hutchison, Collins.
Scotland 1-0 Lithuania, 11 October 2003
Again 11 October brought a vital qualifier Scotland's way.
Berti Vogts' team did well to keep up with Germany, but both Lithuania and Iceland also made it a difficult group.
After Scotland lost to Lithuania in Kaunas and Germany in Dortmund, second place and a play-off spot was the aim.
The Scots went into the final group game behind Iceland. They needed victory over a Lithuania side that had not only beaten them earlier in the campaign but also drawn with Germany, and also required Iceland to not win in Hamburg.
On a nervy day at Hampden, substitute Darren Fletcher scored the only goal of the game just five minutes after coming on, lashing a volley into the net and securing a play-off spot ahead of Iceland, who lost 3-0 in Germany.
Scotland team: Douglas, McNamara, Naysmith, Dailly, Pressley, Ferguson, Rae, Cameron (Fletcher 65), Miller (Hutchison 65), Crawford, McFadden (Alexander 89).
Scotland 1-0 Netherlands, 15 November 2003
Scotland's win over Lithuania led to a two-legged play-off against the Netherlands for a place at Euro 2004 in Portugal.
It started so well for Vogts' men. James McFadden scored one of the great Scotland goals; exchanging passes with Darren Fletcher before a deflected shot beat goalkeeper Edwin van der Sar.
The Dutch hit the woodwork and twice were denied by goal-line clearances, but Scotland held on for a famous win.
Unfortunately, they could not keep Dick Advocaat's side at bay in the return leg in Amsterdam and a 6-0 defeat ended qualifying hopes in cruel fashion.
Scotland team: Douglas, McNamara, Naysmith, Pressley, Wilkie, Ferguson, Fletcher, Dailly, Dickov (Miller 65), McFadden (Hutchison 89), McCann (Pearson 70).
Scotland 1-2 Italy, 17 November 2007
There has not been a build-up like it before or since.
In what was meant to be a 'group of death', Scotland more than held their own and victory home and away against France, as well as a home win over Ukraine, had qualification within their grasp.
However, a loss to Georgia damaged hopes, and now a win was needed against the world champions Italy to guarantee qualification.
By the time Ronnie Brown had finished singing Flower of Scotland, Hampden was rocking, but Luca Toni took just four minutes to put the visitors in front.
Barry Ferguson drew Scotland level, but Christian Panucci's late winner broke the hearts of a nation.
Scotland team: Gordon, Hutton, Naysmith, McManus, Weir, Ferguson, Fletcher, McCulloch (Boyd 90), McFadden, Hartley, Brown (Miller 74).
Scotland 0-1 Netherlands, 9 September 2009
It was a campaign best remembered for Chris Iwelumo's horror miss against Norway, but despite three defeats Scotland went into the final game still with a chance of qualifying for the 2010 World Cup in South Africa.
Only a win against the Netherlands would do to ensure a play-off spot, and George Burley's side rose to the occasion with a stirring display.
Dirk Kuyt struck the Scots' post early on, but then Kenny Miller fired against the crossbar, Steven Naismith hit a post and another Miller effort on the rebound was saved.
Nine minutes from time, with Burley preparing to throw on Garry O'Connor for a late assault on the Dutch goal, David Weir misjudged a long ball and headed into the path of Eljero Elia, who rounded David Marshall to end another qualifying campaign in disappointment.
Scotland team: Marshall, Hutton, Whittaker, McManus, Weir, Brown, Fletcher, Hartley (Commons 66), Miller, Naismith, Maloney (O'Connor 81).