England and Croatia are the favourites to claim the top two positions in this section, but third spot could yet be enough to advance to the round of 16, and Steve Clarke's side will be eyeing a huge three points here.
Monday's clash at Hampden Park will mark Scotland's first match at a major international tournament since the 1998 World Cup, while they are competing in the finals of the European Championship for the first time since Euro 1996, when they also famously took on England in the group stage.
Scotland dramatically qualified for Euro 2020 courtesy of back-to-back penalty-shootout victories over Israel and Serbia in the semi-finals and final of the playoffs.
Clarke's team are certainly outsiders when it comes to claiming a top-two spot in this group, but a win on Monday would place them in an excellent position in the section ahead of the monumental clash with England at Wembley Stadium on June 18.
The Scots will be feeling good about their preparations for this summer's tournament, having picked up a respectable 2-2 draw with the Netherlands in a friendly on June 2 before recording a 1-0 win over Luxembourg on June 6 courtesy of a first-half effort from Che Adams.
Scotland have failed to progress past the group stage in their two previous participations in the European Championship, but Clarke has put together a squad capable of challenging for a spot in the round of 16.
Czech Republic, though, will also certainly have their eyes on a position in the knockout round of the competition and will view Monday's clash with Scotland as key to their chances of progression.
Jaroslav Silhavy's side suffered a 4-0 defeat to Italy in their first pre-tournament friendly on June 4 but managed to return to winning ways on June 8 courtesy of a 3-1 success over Albania.
It is difficult to know exactly what to expect from the Czechs this summer, as they can be inconsistent, but a draw with Belgium in a 2022 World Cup qualifier back in March was an indication of their credentials.
Czech Republic famously finished as runners-up to Germany at Euro 1996, while they made the semi-finals of this competition in 2004 before also claiming a quarter-final spot at Euro 2012 - making them a side more than capable of negotiating their way into the latter stages of the tournament.
Silhavy's team will, rightly or wrongly, view Scotland as their weakest opponents in this group, and the fact that they finish the section with successive matches against Croatia and England means that the 1996 finalists cannot afford a slip up at Hampden Park.
The bulk of the Scotland side for this match is relatively straightforward to select, but there is still some uncertainty over whether Clarke will go with a front two, while the head coach must make a decision on the right-sided centre-back role in what could be a 3-5-2 formation.
Adams and Lyndon Dykes operated as the front two against Luxembourg last time out and that is again expected to be the case for this match, while Kieran Tierney, Andrew Robertson, Scott McTominay and John McGinn are certainties to be named in the first XI.
As for the Czech Republic, West Ham United duo Vladimir Coufal and Tomas Soucek are certainties to feature in their starting XI, while Bristol City's Tomas Kalas will operate in the middle of the defence.
Vladimir Darida - the captain and most experienced player in the squad - will be in the starting side, while Bayer Leverkusen's Patrik Schick, who has struck 11 times at international level, is expected to get the nod over Burnley's Matej Vydra to feature in the centre-forward spot.
Scotland possible starting lineup:
Marshall; Hendry, Hanley, Tierney; O'Donnell, McTominay, McGregor, McGinn, Robertson; Dykes, Adams
Czech Republic possible starting lineup:
Vaclik; Coufal, Celustka, Kalas, Boril; Soucek, Kral; Masopust, Darida, Jankto; Schick
We say: Scotland 1-1 Czech Republic
There is simply no downplaying the importance of this match to both teams, but we are finding it incredibly difficult to separate them. Both are capable of causing problems in the final third of the field, but it might end up being a cagey affair in Glasgow, and we have had to settle on a low-scoring draw.