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.
Full-time in Arnhem. pic.twitter.com/SehtBgUjbw Tottenham Hotspur (@SpursOfficial) October 21, 2021
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.
What does it mean? Spurs winning streak ends as they drop Group G ground
Spurs were unbeaten in the competition coming into this clash in Arnhem, also recording three successive victories across all competitions as they temporarily returned to form.
However, a poor showing against Vitesse ends that run, with Nuno's side falling three points behind group leaders Rennes, who maintained their unbeaten start at the expense of Mura.
Meanwhile, Vitesse sit second in the group on six points with three group-stage games to go.
Danilho Doekhi played an integral role as part of Letsch's dominant three-man defence as he limited Spurs to few chances throughout the game.
The centre-back won seven of his eight duels and was successful in all of his four tackles – a game-leading figure along with Sondre Tronstad.
Dane Scarlett was handed the unenviable task of filling Harry Kane's position up top and the youngster endured a quiet game.
The striker managed just 31 touches before being subbed off – the fewest of any Spurs player to start - and completed just over half of his 10 attempted passes, while collecting an avoidable second-half caution for a foul on Markus Schubert.
Tottenham return to Premier League action with a trip to West Ham on Sunday, while Vitesse host Go Ahead Eagles on the same day.