The match promises to be an emotionally charged occasion – and not just for the potential footballing prize at stake.
It will be Ukraine’s first competitive fixture since the Russian invasion began back in February, which put an immediate stop to their domestic league and forced the national side to pull out of the original date for the play-off fixture in March.
The game was rescheduled for June 1 to allow Ukraine time to prepare and their players have since been able to return to training and take part in friendly matches, beating Borussia Moenchengladbach and Empoli before drawing with Rijeka of Croatia.
While the world sympathises with the plight of Ukrainians – Oleksandr Petrakov's side are likely to have widespread support in their bid to make it to Qatar 2022 – Scotland will have to put sentiment aside in order to keep their own World Cup dreams alive.
Victory over Ukraine would ensure progression to a play-off final against Wales in Cardiff on Sunday, June 5 – and put Steve Clarke’s side just one win away from reaching the finals for the first time since 1998.
Here is how to watch the action …
Who: Scotland v Ukraine
What: World Cup play-off semi-final
Where: Hampden Park, Glasgow
When: Wednesday, June 1, 2022, 7.45pm
Is Scotland v Ukraine on TV?
The match is being broadcast live on Sky Sports Main Event (Sky 401, Virgin 511) and Sky Sports Football (Sky 403, Virgin 513). Coverage gets underway from 7pm.
Subscribers can stream the match using the Sky Go app across all devices. Non-subscribers can purchase a one-off day pass via Now TV for £9.99.
Extended highlights will be shown on Sportscene on BBC One Scotland at 10.40pm.
Scotland will be without Arsenal defender Kieran Tierney who has been left out of the squad after undergoing knee surgery in April.
Wing-back Nathan Patterson had been included in Steven Clarke's pool but has been ruled out of the match, having not played for Everton since April due to ankle surgery.
Ukraine's domestic based players have been preparing for the match at a training base in Slovenia, where they have been joined by star players such as Manchester City’s Oleksandr Zinchenko, Everton’s Vitaliy Mykolenko and Atalanta’s Ruslan Malinovsky following the end of their domestic campaigns.
Scotland and Ukraine have only met twice before, during qualification for Euro 2008. Both matches went the way of the home side with Ukraine claiming a 2-0 win in Kyiv before Scotland won the return game 3-1 at Hampden.
Scotland 6/5, Draw (after 90 minutes) 11/5, Ukraine 5/2 – Bet365