Kick-off on 09.03.23 22:00.

In the playoffs, the Turin team eliminated Nantes. In Turin, the teams played a draw, with Juventus only hitting the target once, resulting in a 1-1 scoreline. In France, Di Maria scored a hat-trick, and the hosts received a red card as early as the 18th minute, resulting in a 3-0 victory. The Breisgau Brazilians topped Group G in the autumn, allowing them to start in the playoffs from the second round.

The Juventus vs. Freiburg match can be watched online. The black and white team had a disappointing performance in the UEFA Champions League. The Zebras hosted PSG, losing 1-2, Maccabi Haifa with a 3-1 win, and Benfica with a 1-2 defeat. Di Maria scored six points in European competitions with goals and assists (3+3), while Vlahović scored four points (2+2). The Bianconeri made their debut at this stage in the 1971/72 season, leaving Vienna's Rapid behind (1-0, 4-1). In the 1974/75 campaign, the Girlfriend of Italy were eliminated by Ajax (1-0, 1-2). In the 1976/77 tournament, the Piedmont team defeated Donetsk's Shakhtar (3-0, 0-1). In the 1988/89 competition, the Turin team overcame Belgian club Liege (1-0, 1-0), and the following year, they defeated Chemnitzer from Germany (1-0, 2-1).

In the 1992/93 tournament, Juve easily defeated Czech team Sigma (2-1, 5-0), and in the 1993/94 UEFA Cup, they eliminated Tenerife (3-0, 1-2). In the 1994/95 campaign, the black and white team defeated Austrian club Admira (2-1, 3-1). In the 1999/00 tournament, the Zebras lost to Celta Vigo (1-0, 0-4), and in the 2009/10 UEFA Europa League, they were defeated by Fulham (3-1, 1-4). The last time the Bianconeri reached this stage was in the 2013/14 competition, when they overcame Fiorentina (1-1, 1-0). The Juventus vs. Freiburg match can be watched online.

The Germans secured away victories against Olympiacos, 3-0, and Nantes, 4-0, in the group stage, and also played a draw with Karabakh, 1-1. Gregoritsch recorded four goal contributions (3+1), while Grifo contributed three (2+1). The team from Baden-Württemberg reached the Round of 16 for the first time.

Prior to this, their highest achievement was reaching the Round of 32 in the 2001/02 UEFA Cup when Braga was eliminated by Feyenoord (0-1, 2-2). The Juventus vs. Freiburg clash can be watched online.