Atletico Madrid's UEFA Champions League hopes were severely dented as they struggled to a poor 0-0 draw away to 10-man Qarabag.
Antoine Griezmann squandered the best chance of a first half that was lacking in drama as Atletico's winless run in the Champions League this campaign continued.
Qarabag, making their first appearance in the UCL this season, looked the more threatening team after the break until forward Dino Ndlovu was sent off after receiving a second yellow card for diving with 15 minutes remaining.
That prompted a late spell of Atletico pressure, but the side from Azerbaijan held on to claim their first point in the competition.
The shock draw leaves Diego Simeone's side struggling on two points from their first three matches, with Group C leaders Chelsea and second-placed Roma to play later on Thursday (AEDT). Atleti are without a win in four across all competitions.
After a quiet opening 25 minutes in the first competitive meeting between the two sides passed without a chance being created, Atletico threatened first when Filipe Luis' cut-back led to Nicolas Gaitan blazing over from 12 yards.
An even better opportunity went begging when Yannick Carrasco raced clear after getting the better of defender Maksim Medvedev, but he was denied by Ibrahim Sehic, as the Qarabag goalkeeper rushed out to save.
Saul Niguez's header was kept out, before a glorious chance went begging when Kevin Gameiro slipped Griezmann through on goal at the second attempt, only for the France international to fail to find the bottom corner, with Sehic getting down to make an excellent reaction stop.
Jose Gimenez volleyed wide from the resulting corner, with Qarabag satisfied to reach the interval on level terms.
It was Qarabag who made the better start to the second half, and Ndlovu was angry to have a penalty claim turned down under pressure from Sime Vrsaljko just outside the penalty area, while Richard Almeida had a deflected effort saved by Jan Oblak.
Simeone brought on Thomas Partey, Angel Correa and Fernando Torres in a bid to change the momentum, but Ndlovu fired narrowly over as the hosts continued to threaten an upset.
Ndlovu – booked earlier in the second half for a foul on Carrasco - claimed for a spot-kick again with 15 minutes remaining but earned himself a second yellow card after what referee Ruddy Buquet deemed to be an over the top reaction to a challenge from Diego Godin, although there did look to be contact.
Atletico pressed for a winner with the numerical advantage and came close to making a breakthrough with six minutes remaining.
Griezmann had a tame shot poorly dealt with by Sehic, allowing Gabi to gather the rebound and cross for Torres, who could not find the target with a header from inside the six-yard box, the striker claiming he was shoved by recovering defender Ansi Agolli as a frustrating evening for the visitors drew to a close.