Scotland begin their World Cup play-off campaign against Ukraine on Wednesday.
The winners of the Hampden semi-final will take on Wales in Cardiff on Sunday for a place in the Qatar finals.
Here, we look back on Scotland’s previous play-off challenges.
Scotland 2 Czechoslovakia 4 (1961)
The two teams met in Brussels in a one-off encounter to see who reached the following year’s World Cup finals after both finished on six points in their qualifying group, which also featured the Republic of Ireland. Ian St John twice gave Scotland the lead but Czechoslovakia took the game to extra time with a controversial late goal after a shot bounced off the underside of the bar and down near the line. Still angered by the equaliser, Scotland midfielders Paddy Crerand and Jim Baxter bizarrely fought over a sponge before the extra 30 minutes started. John White hit the bar, but a Scotland team missing the injured Bill Brown, Billy McNeill, Duncan Mackay, Alex Scott and Davie Wilson ultimately missed out to a side that lost to Brazil in the final in Chile the following year.
Scotland 2 Australia 0 (1985)
Scotland pipped Wales to second spot in their World Cup qualifying group behind Spain to set up a play-off against the winners of the Oceania section. Davie Cooper drilled home a free-kick and Kenny Dalglish set up Frank McAvennie to seal a first-leg win for new boss Alex Ferguson at Hampden. Scotland finished off the job with a goalless draw in Melbourne.
Scotland 1 England 2 (1999)
Scotland came close to upsetting Kevin Keegan’s England side in this Euro 2000 play-off despite suffering a 2-0 first-leg defeat. With Scotland missing freshly injured holding midfielder Paul Lambert, Paul Scholes twice escaped his marker to score at Hampden. Billy Dodds hit the bar and Kevin Gallacher scuffed a good chance in a tight affair, and Scotland were written off ahead of the trip to Wembley. But Don Hutchison headed them into a half-time lead and England needed a brilliant reaction stop from David Seaman to prevent Christian Dailly taking the game to extra time.
Scotland 1 Holland 6 (2003)
James McFadden combined well with Darren Fletcher to fire Scotland to a memorable Hampden win against Dick Advocaat’s side in the first leg of the European Championship qualifier. The Dutch romped home in Amsterdam four days later though, with Ruud Van Nistelrooy grabbing a hat-trick and former Rangers defender Frank De Boer also on target.
Euro 2020 play-offs
Scotland succeeded in their first two penalty shoot-outs to reach the delayed European Championship finals. Steve Clarke’s side beat Israel 5-3 on spot-kicks following a tight and goalless semi-final at Hampden in October 2020 with David Marshall proving the hero by saving from Eran Zahavi. Marshall again stole the headlines against Serbia the following month by denying Aleksandar Mitrovic to seal a 5-4 triumph after a 1-1 draw in Belgrade. Ryan Christie had given the Scots a deserved lead but they had to survive extra-time, with key attacking players already substituted before Luka Jovic’s 90th-minute equaliser.