Tottenham's hopes of winning a trophy this season suffered another setback after they lost 1-0 in the first leg of their Europa League last-32 tie against Gent.
Having slipped to a 2-0 defeat against Liverpool in the Premier League, Spurs were keen to revive their quest for silverware in Europe but came up against a determined Gent side with an appetite for an upset.
In a game of few chances, Gent did enough to deny Harry Kane and Dele Alli the openings they thrive on in the Spurs attack, and striker Jeremy Perbet made no mistake when given the opportunity to score after 58 minutes.
The result extended Tottenham's record of never having won in Belgium, and Mauricio Pochettino's men face an uphill task in the return leg at Wembley - a venue that has not been a happy hunting ground for them in Europe this season.
Gent coach Hein Vanhaezebrouck, whose side sit eighth in the Belgian First Division A, will have been delighted to see the hosts earn a deserved win without star striker Kalifa Coulibaly, who watched from the bench.
Gent burst out of the blocks and swept the ball into Tottenham's penalty area in the opening minute, but the Premier League side soon began to dictate the play with academy graduate Harry Winks taking charge in midfield.
Gent's robust midfield battled hard for a share of possession and Thomas Foket created the home side's first chance when his cross picked out Stefan Mitrovic, who lofted an effort over from close range.
Mousa Dembele powered into the box and found Alli but the England international was crowded out when he attempted to shoot and the first half ended with Gent passing and retaining the ball effectively despite creating few clear chances.
Kane hit the outside of the post with a shot on the turn and Dembele stung the palms of Kalinic as Spurs pressed for an opener early in the second half.
The quality in Pochettino's team began to show in the way Spurs controlled the second half, but both Alli and Kane were frustrated when they tried to find space in attacking areas.
Just as the visitors looked most likely to break the deadlock, they were undone by a Nana Asare pass to Danijel Milicevic, who ran in behind the Spurs defence and squared the ball to Perbet to shoot into the bottom-right corner.
Milicevic went agonisingly close to doubling Gent's lead when Toby Alderweireld yielded possession on the edge of his own box, but fortunately for the Belgian defender Hugo Lloris pulled off a fine one-handed save to keep Spurs' deficit at one goal going into a tricky second leg.