Borussia Monchengladbach's UEFA Champions League aspirations have been dealt a major blow after Freiburg inflicted a 1-0 defeat in the Bundesliga on Friday.
Gladbach were generally the livelier of the two sides in attack, but they failed to make the most of their chances and Freiburg snatched a hard-fought win, giving Bayer Leverkusen and RB Leipzig the advantage in the three-way battle for third and fourth.
Alexander Schwolow in the Freiburg goal was a frequent cause of frustration for Marco Rose's men, particularly in the first half, while Florian Neuhaus had a goal wiped out after straying offside.
The second period also looked like being Gladbach's to control initially, but substitute Nils Petersen nodded in the winner with 58 minutes played, and Alassane Plea's dismissal for two bookings effectively ended the away side's chances.
Gladbach were fortunate to avoid an early blow when, with just 10 minutes played, Luca Waldschmidt met Christian Gunter's left-wing delivery and he steered his first-time effort over from 12 yards.
The visitors responded and nearly netted soon after, as Schwolow thwarted Plea and then also blocked Lars Stindl's subsequent effort on the follow-up.
Gladbach did find the net in the 26th minute, though the goal was disallowed as Neuhaus – who then missed from close range a little later – nudged in Patrick Hermann's strike despite being offside.
Yann Sommer had to be alert at the other end just before the break, parrying Lucas Holer's fierce drive after a counter.
Gladbach seemed up ante after the interval, creating a couple of openings within 10 minutes of the restart, but Hermann headed over and then Philipp Lienhart made a crucial intervention to stop Marcus Thuram tapping in Hermann's cross.
Freiburg capitalised on those previous let-offs just before the hour – Petersen nodding in Vincenzo Grifo's free-kick delivery with his first touch just 63 seconds after replacing Roland Sallai.
Life soon got even trickier for Gladbach, as Plea was shown a second yellow card for catching Robin Koch, and sporting director Max Eberl was also given his marching orders for his remonstrations.
A marvellous late Sommer save to deny Holer kept Gladbach in the contest, but they could not grab an equaliser.
What does it mean? Advantage Leverkusen
With most expecting Leipzig to take third spot, it is largely thought one of Gladbach or Leverkusen will finish fourth – on the back of this result, Peter Bosz's men appear to have a wonderful chance.
However, Gladbach can console themselves with the fact Leverkusen's game in hand on Saturday is at home to in-form pacesetters Bayern Munich, so a positive result is by no means a given
Schwolow shields impressively
It was a contest in which individuals struggled to stand out, but Freiburg goalkeeper Schwolow enjoyed a very effective match between the posts, proving dependable on several crosses and making three saves.
Thuram struggles to provide the spark
While he did make two key passes, generally Thuram had immense difficulty against the Freiburg defence. He was nowhere near as sharp and decisive as he can be.
Gladbach face a trip to Bayern a week on Saturday in a real test of their top-four credentials. Freiburg go to Wolfsburg the same day.