Andy Robertson vs Andriy Yarmolenko
THERE are few players who have come out on top when going up against Scotland captain Robertson in recent years. The left-back is well within the discussion for best full-back on the planet so will have little fear at Hampden.
However, his opponent is a player capable of some real moments of magic. Robertson will be fairly familiar with Yarmolenko who played for West Ham last season. But the winger is on another level for his country holding a talismanic status in the national side.
It's crucial Robertson keeps the winger quiet at Hampden and pins him back with attacks of his own down the left flank forcing him to defend rather than giving him the chance to threaten.
John McGinn vs Taras Stepanenko
Another crucial head-to-head will come in midfield with Aston Villa star McGinn, barring injury, a seemingly guaranteed starter. The former Hibs and St Mirren man has shown his ability to thrive in a number of roles in the national side but could again be asked to play further forward for Steve Clarke's side tonight.
If that is the case then McGinn is likely to come up against defensive-minded Stepanenko. It would come as little surprise if the Shakhtar midfielder was tasked solely with managing McGinn for a long 90 minutes in Glasgow.
If McGinn can evade the grasp of the 6ft 1' holding midfielder it'll disrupt the Ukraine system and could impact midfield partner Ruslan Malinovskyi who has the ability to dictate matches with Stepanenko snuffing out any danger.
Lyndon Dykes vs Sergiy Kryvtsov
Ukraine defender Kryvtsov is a real experienced player on the international stage coming through the age groups for his country. With 30 caps to his name so far - with his first in 2011 - Kryvstov will provide a stern test for Dykes.
When available, QPR striker Dykes has been a tremendous focal point for Clarke's side and offers an out-ball if the defence come under pressure. Dykes has also shown real skill in his link-up play and he'll need to come out on top physically against Kryvtsov to help pull Scotland up the park.
Krystov has played a central role for Ukraine in both four-back and five-back systems in the past which could force Scotland to boost attacking support if Dykes is outnumbered by a resolute Ukraine rearguard.