Having both already negotiated three rounds of qualifying in the Europa League, Legia Warsaw and Rangers face each other in the play-off round with the group stage and the competition proper in their sights.
The Polish runners-up have made a steady start to their Ekstraklasa campaign, currently sitting in eighth on seven points from four games, having lost their opening match at home to Pogon Szczecin.
So far in Europe, Aleksandar Vukovic's side have seen off College Europa (3-0), KuPS (1-0) and Atromitos (2-0) to reach the play-off round.
As for Rangers, they are currently second in the Scottish Premiership with two wins from two and have already overcome St Joseph's (10-0), Progres (2-0) and Midtjylland (7-3).
This fixture will mark the first competitive meeting between the two sides as they clash at the Polish Army Stadium.
Legia will be without French forward Vamara Sanogo who is out with a knee injury, whilst, the 54-time Scottish champions have no fresh injury concerns or suspensions. However, new signing Andy King could make his debut having joined on-loan from Leicester City.
Predicted Line-ups
Legia Warsaw: Majecki; Vesovic, Jedrzejczyk, Lewczuk, Obradovic; Agra, Martins, Cafu, Gvilia, Novikovas; Carlitos
Rangers: McGregor; Tavernier, Goldson, Helander, Barisic; King, Arfield, Davis; Ojo, Morelos, Murphy
Key Clash - Jedrzejczyk/Lewczuk v Morelos
Experienced centre-halves Artur Jedrzejczyk and Igor Lewczuk have built a strong pairing since the latter joined on a free from Bordeaux this summer.
The pair have kept eight clean sheets across Legia's ten competitive ties so far this campaign and appear a stern test for Alfredo Morelos if the Colombian hopes to add to his nine goals in eight games already this season.
The Rangers forward does have a short fuse, however, and can be rash when he becomes frustrated so this could prove to be a key component in the match if the Legia back two can cope with his pace and movement.
What they said
Legia owner and president Dariusz Mioduski expects a tight match between the two clubs, with his squad enduring a large overhaul since the end of the 2018/19 season.
He told Sportsound that "We don't really know the potential of our team. It's a fairly new team with a number of changes. Last year we had nine players whose contracts were expiring and leaving the club so we were bringing new players in during this window and introducing young players from our academy into the squad.
So it's a work in progress, it could be a nice surprise or it could be really difficult. I think it's close to a 50/50 tie, but I think it may be Rangers who are the favourites."