Tottenham slipped to an unlikely defeat as Royal Antwerp recorded a 1-0 victory in their Group J encounter of the Europa League at Bosuilstadion.
Jose Mourinho made nine changes to his side for the game in Belgium but was still able to name a strong side.
Dele Alli was handed just his third start of the season, while the likes of Gareth Bale, Carlos Vinicius, Steven Bergwijn, Giovani Lo Celso and Harry Winks all started.
The Belgian side named former Manchester United and Leicester defender Ritchie De Laet in their starting XI.
Tottenham made a bright start with Bale firing wide and Giovani Lo Celso also testing the Antwerp keeper.
However, it was the Belgians who struck what was to prove the winner when Israeli star Lior Refaelov opened the scoring after 29 minutes.
The goal was created by Dieumerci Mbokani, who robbed Ben Davies of possession and played in Refaelov to rifle home.
Mourinho had seen enough at half-time and made four changes. Son Heung-min, Erik Lamela, Lucas Moura and Pierre-Emile Hojbjerg came on for Vinicius, Alli, Bergiwjn and Lo Celso.
Bale off, Kane on
The fifth and final substitute arrived for Spurs just short of the hour mark. That was when Bale left the field to be replaced by Harry Kane.
If the Portuguese was doing it for effect, then it did not have the desired one as Antwerp should have extended their lead.
Harry Winks’ dreadful backpass played Refaelov in and only a goalsaving block by Davinson Sanchez stopped the Israeli doubling his tally.
They had another let-off five minutes later as Mbokani inexplicably blazed over from two yards out after Koji Miyoshi’s cross had laid it on a plate for him.
Mourinho then turned to Kane just before the hour, replacing Bale, and the dynamic of the game changed.
Son had an effort blocked by Abdoulaye Seck as Spurs began to press while Erik Lamela could not get on the end of a dangerous cross.
But it was Antwerp who continued to have the best chances as they sliced Spurs open on the break.
Simen Juklerod had a golden opportunity as he raced clear on goal, but he blazed over and then Birger Verstraete saw an effort blocked.
Spurs never threatened an equaliser, despite some late territorial, and continue a quirky record of never having won in Belgium.
The win sends Antwerp top of the group though there remains time for Spurs to bounce back and progress too in the Europa League.