Tottenham's Europa League hopes have been dealt a blow after Jeremy Perbet's goal gave Gent a surprise victory in their last-32 first-leg meeting.
French striker Perbet controlled and slotted into the corner from Danijel Milicevic's pull-back on the hour.
A strong Spurs line-up were poor for most of the evening, although Harry Kane clipped the post after half-time.
Gent, eighth in the Belgian league, almost added a second as Milicevic's shot was tipped on to the post.
The second leg is at Wembley on Thursday, 23 February.
Spurs stutter to surprise defeat
Gent's 20,000-capacity stadium, the Ghelamco Arena, is host to a Michelin-starred restaurant, but there was little to feast on for Tottenham, who turned in a strangely listless performance.
Mauricio Pochettino had spoken before the match about how keen his players were to put behind them a poor display in losing 2-0 at Liverpool in the Premier League on Saturday.
With that in mind, Pochettino selected a very strong side - with only two changes to the team beaten at Anfield.
Dele Alli skimmed an early shot wide from just outside the penalty area after good build-up involving Harry Winks and Ben Davies, but that was as good as it got in the opening half.
Pochettino's decision to move midfielder Moussa Sissoko out to the left at half-time led to a lively spell from the visitors, during which Kane clipped the post.
But Sissoko looked increasingly lost, and the Tottenham head coach was prompted into more tactical tweaks in an attempt to find an equaliser.
Nothing worked - and Tottenham's frustration was summed up as Alli picked up a needless yellow card for dissent.
Wembley worries ahead for Pochettino
The Gent fans were singing "we're going to Wembley" during the second half, in anticipation of next week's second leg at England's national stadium.
They may have more reason than Tottenham to look forward to their big night in north London.
Spurs stumbled at their temporary European home in this season's Champions League - failing to qualify from their group after losing at home to Monaco and Bayer Leverkusen.
Having gone into the match in Belgium as second-favourites to win the Europa League, behind only Manchester United, Pochettino's team now need a good Wembley performance just to stay in the competition.
Perbet proves a pointGent boss Hein Vanhaezebrouck - celebrating his 53rd birthday - caused something of a surprise with his team selection, making five changes and leaving his 15-goal top scorer Kalifa Coulibaly on the bench.
It suggested that Vanhaezebrouck was prioritising a top-six Belgian league place - and qualification for the domestic championship play-offs - above European progress.
Yet his decision to select the 32-year-old journeyman Perbet in attack paid off handsomely.
Even before Gent took the lead, the players selected were full of energy, pressing Tottenham into mistakes and enjoying plenty of possession.
They created decent openings; centre-back Samuel Gigot shanked an effort wide from the edge of the penalty area, while Toby Alderweireld had to block a shot from midfielder Kenny Saief, who made an adventurous run from the left after a poor Kyle Walker pass.
Better chances came after half-time, with Milicevic slicing wide as Spurs switched off at a throw-in moments before Perbet's goal, and unmarked centre-back Stefan Mitrovic spurning an opportunity to make it 2-0 as he headed over from a corner.
Man of the match - Danijel Milicevic (Gent)
'We didn't create enough chances'
Tottenham defender Eric Dier told BT Sport: "We did show more aggression than Saturday against Liverpool. I don't think we created enough chances to win.
"In the first half, they were the better of the two sides but after half-time we were better until the goal. It stopped us in our tracks. We could not get going again. They sat back and we could not get the away goal.
"When you go a goal down, you want to give everything to get back into the game. Maybe we were erratic at times and could have been a bit calmer and waited for our chance. That is something for us to work on.
"I don't see why we cannot turn it around. This team gave everything against us, we did that but lacked a bit of quality. At home we will be better."
Tottenham's Belgian blank - the key stats
- This was the seventh consecutive first leg of a knockout match that Tottenham have failed to win in the Europa League (drawing three, losing four).
- Tottenham have never won a European match in Belgium (two draws, three defeats).
- Spurs have lost back-to-back matches in the Europa League for the first time since November 2011.
- Jeremy Perbet's goal was Gent's first shot on target in the match in the 59th minute.
- Perbet has scored in two of his last three home Europa League appearances for Gent.
- Spurs have now scored only one goal in their last four games in all competitions, having scored 12 in the four prior to this run.
- Of the last eight matches in which Tottenham have failed to score, four have been in European games.
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