Tottenham's bright start to the season suffered a bump in the road as they were beaten 1-0 by Royal Antwerp in the Europa League.
The Belgian league leaders came into this clash on a five-match winning streak and made Jose Mourinho's side look distinctly ordinary with Lior Refaelov (28) grabbing the winning goal after an error by Ben Davies.
Mourinho made nine changes from the win at Burnley, hoping to see some of his fringe players stake a claim but it was a flat display that triggered Mourinho to make four changes at half-time with Dele Alli, Steven Bergwijn, Vinicius and Giovani Lo Celso all hooked.
Gareth Bale looked short of fitness, being replaced by Harry Kane on 58 minutes. Even the introduction of their talisman could not spark Spurs into life, with the Belgians unfortunate not to extend their lead in the second half.
Antwerp: Butez (7), De Laet (8), Gelin (7), Seck (7), Juklerod (7), Hongla (7), Haroun (7), Gerkens (7), Miyoshi (7), Mbokani (8), Refaelov (8)
Subs: Buta (7), Benavente (6), Verstraete (6)
Tottenham: Lloris (6), Aurier (6), Sanchez (5), Davies (4), Reguilon (6), Winks (6), Dele (4), Lo Celso (6), Bergwijn (5), Bale (5), Vinicius (6)
Subs: Son (7), Kane (6), Moura (7), Lamela (6), Hojberg (7)
Man of the match:Ritchie De Laet
How Spurs met defeat in Belgium...
All eyes were on Bale with Mourinho saying he was going to let him "fly" in the Group J encounter between the top two. The Welshman and his teammates saw plenty of the ball but it all came in deep, unthreatening areas as Spurs looked a shadow of the team that beat Manchester United 6-1.
Bale fired an ambitious effort well wide, Lo Celso's curled one effort straight at goalkeeper Jean Butez in the opening exchanges but that was as good as it got for the half.
Antwerp carried a greater threat than their so-called more illustrious counterparts and took the lead in 29 minutes.
Davies was at fault as he was caught in possession by former Norwich striker Dieumerci Mbokani and he raced away, teeing up Refaelov, who stayed very calm to power a finish into the roof of the net.
A response would have been expected by Mourinho but the lack of intensity in Spurs' game continued. Mourinho did not like what he saw and Alli was one of four men hauled off at the break, the second time in three starts this season he has not made it out for the second half.
Although there was a better rhythm to what Spurs were producing, it was Antwerp that really should have extended their lead when Mbokani somehow blazed over from two yards out after Koji Miyoshi's cross had seemingly presented him with an unmissable chance.
Mourinho then turned to Kane just before the hour, replacing a non-existent and half-baked Bale.
But it was Antwerp who continued to have the best chances as they sliced Spurs open on the break.
The impressive Simen Juklerod had a golden opportunity as he raced clear on goal but couldn't test Hugo Lloris with a wild finish.
Those missed chances didn't come back to bite the Belgians though. Spurs carried little threat - even with Kane providing a decent focal point. He couldn't spare Tottenham's blushes as they were beaten for the first time in 10 games.
Man of the match: Ritchie De Laet
He was the only Premier League winner on the pitch and the former Leicester City defender showed why with a performance full of discipline and defensive brilliance at the heart of the defence. De Laet played 12 Premier League games for Leicester in the 2015/16 season before being sent out on loan to Middlesbrough, where he did the unprecedented double of also winning promotion with the Championship side. He's a player made for the big occasion.
- Spurs have never won away to Belgian opposition (P6 D2 L4), losing on each of their last three visits.
- Royal Antwerp are the first Belgian side to beat English opposition in European competition since KAA Gent beat Tottenham in the Europa League in February 2017 (Belgian sides were winless in nine such matches prior to today).
- This was Mourinho's first defeat in a Europa League game since November 2016 (a 2-1 defeat to Fenerbahçe), ending a 12-match unbeaten run for the Portuguese manager in the competition.
Spurs are back in Premier League action on Sunday with a home fixture against Brighton (kick off 7.15pm) before heading off to Bulgaria for a Europa League clash with Ludogorets next Thursday.