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.
Nashville SC v San Jose Earthquakes: ‘A win would change everything’ - Godoy
Anibal Godoy insists that Nashville are already looking at their game against San Jose Earthquakes on Saturday as a must-win.
Nashville have won just once in the MLS this season and sit in 14th place in the Eastern Conference after a run of four without a win.
The Earthquakes, meanwhile, are bottom of the Western Conference having lost eight of their matches and recording just one win.
Godoy is aware of how their poor start to the season could affect their playoff hopes later down the line but is confident that Nashville can turn things around.
He said: “For us, it's an important week. It's a day we have to win, or we'll start to feel the pressure from other teams as they start to separate in the table.
“This league is long but if we want to get to the playoff you have to win games early on, especially at home.”
Liverpool agree compensation deal for Slot
Liverpool and Feyenoord have reached an agreement in principle over a compensation deal for Arne Slot to become the Reds’ manager next season, according to widespread Dutch media reports.
The Dutchman is reportedly poised to take over from Jurgen Klopp, who announced in January that he would be leaving the club at the end of the campaign.
Slot led Feyenoord to their second Eredivisie title last season after taking over the club in 2021.
It is believed that he topped the list of Liverpool’s favoured candidates due to his attacking playing style and ability to develop players.
Former Liverpool midfielder, Xabi Alonso, who led Bayer Leverkusen to their first Bundesliga title, and Sporting CP’s Ruben Amorim were also reported contenders to take over from Klopp.
Slot had already confirmed his interest in managing in the Premier League, both earlier this week and previously when he was linked to Tottenham in 2023.
QPR 4-0 Leeds United: Shock loss for Farke's men seals Leicester's promotion
QPR thrashed Leeds United 4-0 in the Championship on Friday, ensuring Leicester City booked their promotion straight back to the Premier League.
Ilias Chair was the star for the Hoops as he scored the opener and assisted two more goals to ensure QPR will stay in the Championship for another season.
Lucas Andersen, Lyndon Dykes and Sam Field also got their names on the scoresheet in an emphatic win for Marti Cifuentes' side.
Leeds' heaviest defeat of the season was a huge blow in the race for an automatic promotion spot, with Ipswich Town just one point behind them in third place with two games in hand going into their away clash against Hull City on Saturday.
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