Fenerbahçe's nearly 15-year wait for UEFA Champions League will continue after the Istanbul-based side suffered a 2-1 defeat against Dynamo Kyiv in the second round qualifiers Wednesday.
The match was decided in extra time after neither team was able to break the deadlock in the first half.
The Yellow Canaries made a bright start in front of their home crowd and dominated much of the first 45 minutes, creating opportunities to score on several occasions.
In the 10th minute, Joshua King's goal was disallowed by Italian referee Massimiliano Irrati due to a foul by Enner Valencia, who had made the assist.
Diego Rossi then shot over the bar on two occasions and Valencia also wasted a couple of positions.
Fenerbahçe was also denied by the post in the 20th minute when Irfan Can Kahveci's free kick from outside the penalty arc ricocheted out.
Kyiv's first shot on target came in the 45th minute as Vladyslav Dubinchak tried his luck from a distance, but the ball whistled over the crossbar. The first half ended 0-0.
The second half started off with one change from Fenerbahçe. Coach Jorge Jesus brought on new signing Emre Mor for Kahveci.
However, the Istanbul side was down to 10 men after Ismail Yüksek was shown a second yellow in the 54th minute.
The dismissal became the match's turning point as Fenerbahçe conceded just three minutes later.
Vitaliy Buyalskyi opened the scoring with a close-range finish in the 57th minute for Dynamo Kyiv.
Despite being down to 10 men, Fenerbahçe piled on the pressure and earned a penalty in the 69th minute.
Valencia stepped up for the spot kick but was denied by Kyiv goalkeeper Heorhiy Bushchan.
Fener nevertheless leveled the score late in the game when Hungarian defender Attila Szalai scored in the 89th minute with a great header.
The late equalizer sent the match to extra time where both teams played with caution and came close on several occasions.
Kyiv defender Oleksandr Karavayev, however, scored a late winner in the 114th minute sending his side to the Champion League third qualifying round.
Fenerbahçe, on the other hand, will now compete in the Europa League third qualifying round.
It will now face Czech side Slovacko for the first leg on Aug. 4 and the second leg match is scheduled for Aug. 11.
The Istanbul-based team also has the likelihood of ending up in the third-tier Europa Conference League, if it is eliminated in the Europa League third qualifying round.
It will in that case move to the UEFA Conference League playoffs round.