Fenerbahçe threw everything at it – overturning a 3-1 deficit, dominating Rangers at Ibrox and forcing extra time – but when the dust settled, the Scottish giants prevailed 3-2 in a dramatic penalty shootout.
Jose Mourinho's side delivered a tactical masterclass, stifling Rangers and seizing control through Sebastian Szymanski's inspired performance.
Yet, despite a 2-0 win on the night, fate and the penalty lottery sent Fenerbahçe crashing out of Europe.
Fenerbahçe started cautiously, wary of Rangers' attacking firepower.
Their defensive discipline paid off, limiting the home side to half-chances while probing with long balls behind the Scottish defense.
Then, on the stroke of halftime, Szymanski produced a moment of brilliance.
The Polish midfielder latched onto a loose ball and hooked a stunning volley past Jack Butland to give Fenerbahçe a 1-0 lead.
Rangers, rattled by the goal, struggled to regain their composure after the break. Mourinho's side sensed blood.
They pressed high, forced turnovers, and created multiple chances through Talisca, who came close twice but couldn't find the net.
Finally, in the 73rd minute, Szymanski struck again, poking the ball past Butland to level the tie on aggregate. Fenerbahçe were in full control, but their inability to kill the game would come back to haunt them.
Extra time saw the Turkish side continue their dominance.
They carved out more openings, denied Rangers clear-cut chances, and appeared poised to complete an epic comeback.
But luck was not on their side.
Mert Hakan Yandaş went down in the box after a challenge from Nicolas Raskin, but referee Slavko Vincic waved away the appeals, leaving Mourinho furious on the touchline.
The decision loomed large as penalties became inevitable.
With the shootout underway, disaster struck early for Fenerbahçe.
Dusan Tadic's opening penalty was saved by Butland's outstretched legs, setting the tone.
Irfan Can Egribayat briefly gave his side hope by turning Ianis Hagi’s effort onto the post, but Butland emerged as the hero, stopping Fred’s shot before Yandaş sent his attempt over the bar, sealing Fenerbahçe's fate.
A defiant Mourinho held nothing back in his post-match remarks.
"We did everything to win. The referee and VAR decided we should go to penalties," he told TNT Sports. "In Istanbul, we made mistakes and deserved to lose. Tonight, we were the better team by far."
The Portuguese coach, visibly frustrated, suggested that his side had suffered from officiating decisions throughout their European campaign.
"I won’t say what I really think because I don’t want a UEFA ban. But I hope what happened tonight wasn’t a consequence of last year’s Budapest final. We’ve faced strange decisions all season – whether against Lille, Manchester United, or tonight."
Mourinho, however, stood by his players. "I’m proud of them. They gave everything. If we had advanced, I wouldn’t have felt prouder than I do now. We lost together, not just the ones who missed penalties."
For Szymanski, it was a bittersweet night.
The Polish midfielder, who had struggled to find his scoring touch in Europe this season, delivered a performance to remember.
His brace, coming at a crucial moment, showcased the talent that made him one of Fenerbahçe’s most valuable assets. Yet, his heroics weren’t enough to secure passage to the quarterfinals.
Szymanski had only managed two goals in the Turkish league and one in the Champions League qualifiers before this match.
But on the big stage at Ibrox, he finally found his European breakthrough. Unfortunately for Fenerbahçe, his efforts were overshadowed by the cruel nature of penalties.
Adding to the heartbreak, national team defender Mert Müldür suffered an injury late in the match.
The 25-year-old limped off in the 85th minute before collapsing in the 87th, forcing Mourinho to make a last-minute substitution.
Alexander Djiku replaced him, but Müldür’s injury further compounded the disappointment for the visitors.
For Rangers, this was a night of resilience.
Interim boss Barry Ferguson, leading the team after Philippe Clement’s departure, praised his squad’s grit. "We believed we'd get it done. We could have been more clinical, but we deserved this."
The Scottish club, twice runners-up in the competition, now face Athletic Bilbao in the quarterfinals, aiming to salvage their season after a turbulent domestic campaign.
