Maximilian Wittek's second-half strike condemned an insipid Tottenham to a 1-0 loss against Vitesse in the Europa Conference League.
Spurs had won just two of their last seven away games in European competition before Thursday and their struggles on the road showed in a timid opening 45-minute showing.
However, the visitors were unfortunate to not go ahead after the interval at the GelreDome as Bryan Gil rifled onto the woodwork in an otherwise uneventful first hour of football.
Nuno Espirito Santo's side, who rested Harry Kane entirely for the trip to Holland, were eventually made to pay for their lacklustre performance when Wittek drilled in from the edge of the area to end Spurs' unbeaten start in the competition and leave them third in Group G.
Pierluigi Gollini smothered the first chance of the game as he raced out to deny Nikolai Baden Frederiksen before Jacob Rasmussen flicked narrowly wide following Wittek's corner.
Nuno's side could not manage a shot on target in the first half but went in level at the break after Thomas Letsch's team failed to make the most of their control of proceedings.
Spurs duly returned after the interval with greater attacking impetus, Bryan rattling the crossbar with a left-footed curler just two minutes into the second half.
Eli Dasa then drove narrowly wide of the right-hand post before forcing another save from Gollini as Vitesse piled on the pressure just past the hour mark in a contest of limited opportunities.
The hosts had scored in each of their last eight games and made it nine when Wittek rifled a left-footed half-volley - via a deflection off Davinson Sanchez - into the bottom-right corner with 13 minutes remaining.
Spurs pressed on for a late equaliser that did not come, meaning their five-game unbeaten run in the Netherlands in the 21st century came to an end.
Hurtig the hero after late goal sends Arsenal into Champions League quarters
Lina Hurtig's 89th minute winner ensured Arsenal progressed to the quarter-finals of the Women's Champions League after edging Juventus 1-0 on Thursday.
After being frustrated for large parts of the encounter, Hurtig bundled home from close range after Martina Lenzini's poor clearance to book the Gunners' place in the last eight.
Despite Arsenal dominating the early exchanges, it was Juventus who had the first sight of goal, though Eva Schatzer's effort was easy for Daphne van Domselaar to gather.
In a first half that saw just two shots on target, both coming from the visitors, Renee Slegers' substitutes proved to be the difference for Arsenal.
Slegers introduced Beth Mead, Stina Blackstenius and Hurtig late on, with the latter somehow putting Kim Little's cross over the bar from five yards out.
However, the Swede would atone for her earlier error, combining with fellow substitute Blackstenius to net against her former club and send them out of the competition with two group games remaining.
Meanwhile, in Group D, Barcelona edged closer to the quarter-finals of the competition with a convincing 4-1 victory over St. Polten at the Generali Arena.
The reigning champions are still three points behind Manchester City following their 2-1 win over Hammarby, and know a win against the Swedes next month will see them progress.
Kika Nazareth opened the scoring in the 20th minute after capitalising on a mistake by Kamila Dubcova, notching her second nine minutes later from close range.
Barca found themselves three goals up at the break when Vicky Lopez netted her first goal in the competition to put the result beyond doubt.
There was also a landmark moment for Alexia Putellas, who netted her 200th goal for the club with a well-taken effort into the far corner.
Valentina Madl took some of the shine off an otherwise impressive display from the visitors, who have now taken their tally to 20 goals from their four matches in the competition.
Guardiola agrees two-year contract extension with Man City
Pep Guardiola will be Manchester City manager for at least two more seasons after 2024-25, after he signed a two-year contract extension on Thursday.
The 53-year-old was coming to the end of his City deal, which was due to expire at the end of the current campaign, but he has opted to remain at the Etihad Stadium.
The deal itself will take Guardiola's tenure at the club to over a decade, making him City's longest-serving manager since Les McDowall in 1963.
There had been suggestions that he may leave at the end of the season following the announcement that director of football Txiki Begiristain was on his way out.
Guardiola was strongly linked with the England job after Gareth Southgate resigned in the wake of their Euro 2024 final defeat, but the Football Association appointed Thomas Tuchel last month.
“Manchester City means so much to me," Guardiola said. “This is my ninth season here; we have experienced so many amazing times together. I have a really special feeling for this football club.
“That is why I am so happy to be staying for another two more seasons.
“Thank you to everyone for continuing to trust and support me – The Owner, The Chairman Khaldoon, Ferran, Txiki, the players and, of course, the fans… everyone connected to Manchester City. It has always been an honour, a pleasure and a privilege to be here.
“I have said this many times before, but I have everything a manager could ever wish for, and I appreciate that so much.
“Hopefully, now we can add more trophies to the ones we have already won. That will be my focus.”
Having been appointed in 2016, Guardiola is by some distance Manchester City's most successful manager of all time, having won 18 major trophies during his time at the club.
That list includes their first-ever Champions League triumph in 2023 and six Premier League titles, including an unprecedented four on the spin.
He also boasts a 72.04% win percentage across all competitions, which is unsurprisingly the highest of any full-time City manager in history.
Shaw at the double as Man City progress in Champions League
Khadija Shaw scored twice as Manchester City beat Hammarby 2-1 to seal their place in the Women's Champions League quarter-finals.
Gareth Taylor's team entered Thursday's game with a perfect record in Group D, and their fourth win in as many European matches ensured they finished in the top two.
Shaw—the leading scorer in the Women's Super League this season with eight goals—put them ahead in the 31st minute, driving into the area after taking in Yui Hasegawa's pass before seeing her shot deflect into the top corner.
Shaw was booked for celebrating in front of the home fans despite appearing to have objects thrown at her from the stands, and Hammarby should have levelled when Julia Blakstad fired wide 10 minutes later.
The hosts did draw level three minutes into the second half as Ellen Wangerheim tapped home while City's Laura Blindkilde Brown was down appealing for a free-kick.
That parity was short-lived, though, as Shaw blasted into the top corner from 25 yards out, taking her overall tally for this season to 12 goals in all competitions.
In Group C, meanwhile, Bayern Munich lost their perfect record as they played out a 1-1 draw with Valerenga, boosting Arsenal's hopes of topping the pile.
Jovana Damnjanovic came off the bench to put Bayern ahead 15 minutes from time in Norway, but Elise Thorsnes headed home following an 88th-minute corner to snatch a point for the hosts.
Arsenal could now move within a point of Bayern when they face Juventus in Group C's other match later on Thursday.
SportsMax is the Caribbean sports channel of choice, committed to providing sporting content of the highest quality to the Caribbean, delivered by a team of highly innovative, passionate and qualified professionals.
(876) 619-7629
digitalmedia@sportsmax.tv
