Gonzalo Castro missed a first-half penalty for Borussia Dortmund as Thomas Tuchel's side suffered a 1-0 friendly loss against 1860 Munich.
A 36th minute goal from Levent Aycicek was enough to condemn last season's Bundesliga runners-up to a shock defeat.
Dortmund, who rested Pierre-Emerick Aubameyang after the star forward netted a brace in Thursday's 3-2 win over St Pauli - made much of the running during the first-half but were let down by a lack of composure on the final ball before passing up a glorious opportunity to lead in the 34th minute.
1860 goalkeeper Jan Zimmermann took a heavy touch inside his own area and brought down Dortmund new boy Sebastian Rode in trying to atone for his error.
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He would do so soon enough by plunging to his right to keep out a poor spot kick from Gonzalo Castro and 1860 were quick to make their visitors pay.
Werder Bremen loanee Aycicek drove towards a flimsy looking Dortmund defence and smashed home confidently from the edge of the area.
Zimmermann continued his erratic afternoon by bringing down Ousmane Dembele after the break – he was punished with a free-kick on the right-hand corner of the area, although replays showed Thomas Tuchel's side should have been awarded a second penalty.
Dortmund were unable to find an equaliser and will fly to China next week to continue their pre-season preparations with friendlies against Manchester United and Manchester City.
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- Goal