These two clubs met in the Champions League group stages just last season, but only one can make it this time.
Back then, they played out a goalless draw in Kyiv, before a 2-0 Benfica victory in Lisbon saw the Portuguese side reach the knockout phase.
A lot has changed in the mean time, not least the fact Ukraine has been invaded by Russia.
As a result of the ongoing conflict, this first leg will be played in Łódź in central Poland.
Given the horrific circumstances, it’s a minor miracle that Dynamo Kyiv are featuring in this tie, having to come through two rounds of qualifying already.
First, the Blue and Whites dumped out Fenerbahçe, winning 2-1 after extra time at Şükrü Saracoğlu Stadium.
Then, in the third qualifying round, Mircea Lucescu’s team were taken to extra time again, this time by Sturm Graz.
Nevertheless, Kostyantyn Vivcharenko and Viktor Tsyhankov both struck in the additional half hour at Liebenauer Stadium as Dynamo won in Austria.
So, this gigantic club from a war-torn country are on the verge of a 19th Champions League group stage appearance, not wanting to add to their seven in the Europa League.
This though will be the toughest assignment they’ve faced so far this season, against a Benfica side cast as the villains.
The Eagles entered in the previous round, demolishing Midtjylland, winning 4-1 at home and then 3-1 in Denmark.
Gonçalo Ramos bagged a hat-trick at Estádio da Luz, while Enzo Fernández scored in both legs.
The Reds qualified for their 17th Champions League group phase last season, also needing to win two qualifiers to achieve that, eventually getting all the way to the quarter-finals.
Now under Roger Schmidt, Benfica are favourites to advance, looking to leave Stadion Miejski ŁKS with a favourable result.