With four divisions separating the two sides, Wolfsburg enter the clash as heavy favourites, but Jena will no doubt provide a stern test.
Match preview
Relegated at the end of the 2019-20 campaign, Jena have been plying their trade in the fourth tier of German football ever since.
Somewhat of a yo-yo side in recent history, Jena have not played higher than the third division since 2008.
Three-time winners of the old East German Championship between 1963 and 1970, a fall from grace saw Jena drop out of the public consciousness.
Despite that, they have been able to compete in the Pokal regularly in recent years, featuring in each of the last two editions.
Unlike other countries in Europe, the Pokal is a distinctly unique competition, as it combines the top teams, with clubs from the regional leagues.
One of those clashes will see Jena take on top-flight Wolfsburg, in a clash that offers up a potential banana skin for the Bundesliga side.
A disappointing campaign in 2021-22 saw Wolfsburg finish outside the top half, ending the season in 12th place.
Arresting such woeful form will be crucial for Wolfsburg this season as they target a return to European football.
Their campaign will start with a trip to face Jena - a side that they last played a competitive fixture against in 1997.
Two-second division sides at the time, Wolfsburg triumphed 4-1 in their last meeting, with the Wolves eyeing up a repeat result this weekend.
Team News
With a clean bill of health heading into the fixture, Wolfsburg boss Niko Kovac will have a full squad to pick from.
Jonas Wind has impressed for Wolfsburg in pre-season and scored during a recent win against Brentford, with the 23-year-old pushing for a starting position.
Expect regular number-one Koen Casteels to start between the sticks for Wolfsburg.
At the opposite end of the pitch, Kevin Kunz is likely to start in net for Jena, with Bastian Strietzel and Burim Halili making up part of the defence.
New arrival Jan Dahlke should lead the line for giant-killing hopefuls Jena.
Carl Zeiss Jena possible starting lineup:
Kunz; Hoppe, Strietzel, Halili, Muiomo; Lämmel, Lange, Schauss; Krauss, Verkamp, Dahlke
Wolfsburg possible starting lineup:
Casteels; Baku, Bornauw, van de Ven, Franjic; Wimmer, Arnold; Waldschmidt, Kruse, Marmoush; L. Nmecha
We say: Carl Zeiss Jena 0-5 Wolfsburg
Wolfsburg will be confident of victory this weekend, regardless of the side that manager Kovac fields.
With what should be a comfortable win for the Wolves, expect the Bundesliga side to prevail comfortably.