Victor Osimhen's first-half brace sent Galatasaray top of the Europa League table after they edged a five-goal thriller against 10-man Tottenham.
The defeat marked Spurs' first of their European campaign, and they could drop out of the top eight should results go against them later on Thursday.
Galatasaray took the lead with six minutes on the clock in stunning fashion. Archie Gray's headed clearance was collected by Yunus Akgun, who rifled a left-footed effort into the top corner.
But Spurs drew level through a surprise inclusion in their starting line-up as Will Lankshear notched his first senior goal with a simple finish from Brennan Johnson's cross.
However, after seeing an effort ruled out a minute earlier for offside, Osimhen put the hosts back in front, prodding the ball home after sloppy play from Radu Dragusin.
Osimhen then doubled his tally six minutes before half-time, combining again with Dries Mertens, this time planting the Belgian's teasing delivery beyond Fraser Forster.
It went from bad to worse for Ange Postecoglou's side on the hour-mark when Lankshear was shown a second yellow card for a mistimed challenge on Gabriel Sara.
Hopes of a Spurs comeback were revived in the 69th minute when substitute Dominic Solanke neatly flicked Pedro Porro's cross into the net, but Galatasaray held on for the win.
Full-time. pic.twitter.com/fwsGZ1ttLb
— Tottenham Hotspur (@SpursOfficial) November 7, 2024
Data Debrief: Turkish delight
While the score-line suggests a tightly contested affair at Rams Park, Galatasaray were worthy winners against Tottenham.
Okan Buruk's side registered 28 shots compared to Tottenham's five, ending the contest with an expected goals (xG) total of 3.28 to their opponents' 1.87.
But having ended the night on a sour note, Tottenham's Lankshear followed in the footsteps of a former Spurs great.
At 19 years and 201 days, he became Tottenham's youngest goalscorer in a major European since Harry Kane (18 years and 140 days) scored against Shamrock Rovers in the 2011-12 Europa League.