Bayern Munich, the defending champions, suffered their initial Bundesliga loss of the season in a resounding defeat to Eintracht Frankfurt.
Omar Marmoush, Eric Ebimbe, and Hugo Larsson quickly established a 3-0 lead for Eintracht within 36 minutes at Deutsche Bank Park.
Despite Joshua Kimmich pulling one back, Frankfurt extended their lead with goals from Ebimbe and Ansgar Knauff.
Bayern, currently in second place, trail three points behind Bayer Leverkusen, who will face third-placed VfB Stuttgart on Sunday.
England captain Harry Kane, who played the entire 90 minutes, failed to score for only the third time in 13 Bundesliga games this season, maintaining his impressive tally of 18 goals from 13 league matches.
Although Frankfurt had not won in their previous three league games, they had the distinction of being the last team to score five goals against Bayern in the Bundesliga, achieving a 5-1 victory in 2019.
Bayern, having secured a spot in the Champions League last 16, will face Manchester United in their upcoming final group game on Tuesday.
For United to advance to the last 16, they need a victory and rely on a draw between Copenhagen and Galatasaray.
In Wednesday’s German Cup match, Frankfurt was eliminated by third-tier Saarbrucken, the same team that defeated Bayern in the second round.
Frankfurt, currently in seventh place, is set to travel to Aberdeen for a Europa Conference League match on Thursday.