Tottenham's continental nightmare took another turn for the worse after they endured a surprise 1-0 defeat to Gent in the last 32 of the Europa League.
After limping out of the Champions League group stage in November, Spurs now have work to do next week at Wembley if they are to avoid an early exit from Europe's second tier tournament, too.
Jeremy Perbet scored the winner just before the hour for Gent, who sit a lowly eighth in Belgium's top tier but who fully deserved their victory against a painfully out-of-sorts Tottenham.
Mauricio Pochettino's men came here hoping to make amends for Saturday's damaging defeat to Liverpool but they leave with only more questions surrounding their worrying dip in form.
After winning seven games in a row at the start of the year, Spurs have now managed just two in their last six as they approach a make-or-break period in their season.
Pochettino seemed to recognise as much by picking a near full-strength team, with Christian Eriksen the only key player left on the bench as Harry Kane, Dele Alli, Mousa Dembele and Toby Alderweireld all started.
The boss had said his players wanted the chance to put right their miserable display at Anfield but perhaps the idea was also to put this tie to bed, with Fulham up next in the FA Cup on Sunday.
Next week's second leg comes three days before Stoke visit in the Premier League.
The plan backfired, however, and Spurs now head to Craven Cottage without the luxury of being able to rest players given they surely need a victory to boost morale.
Some of Tottenham's travelling fans missed the opening 10 minutes after the buses which were supposed to take them to the ground failed to show up, but in truth they could have arrived at half-time and still missed nothing of note.
Spurs were poor in the opening 45 minutes, their performance a collection of stray passes, heavy touches and mistimed tackles, with every mistake handing a fresh injection of belief to their opponents.
Alli drove a shot just wide of the post from 25 yards and Kane tested goalkeeper Lovre Kalinic with another bending effort from distance early on.
But Gent were the better side and could have taken the lead when Samuel Gigot peeled free at the back post, only for the centre-back to slice his half-volley harmlessly wide.
Tottenham, and in particular the energetic Harry Winks, tried to establish some control on proceedings but Davies and Kyle Walker struggled to make any headway out wide as attacks became increasingly narrow, ponderous and predictable.
A drab opening period was summed up when Hugo Lloris sprinted out wide to save the ball bouncing out for a corner, only to slice it behind anyway with his weaker right foot.
Pochettino has not always been the quickest to change tactics during games but the Argentinian twisted at half-time, switching to three in defence with Moussa Sissoko thrown out to left wing-back and Davies shifting inside to left centre-half.
Briefly, it seemed to work as Kane hit the outside of the post with a shot on the turn before teeing up Dembele on the edge of the box soon after but the midfielder scuffed wide.
Any gathering momentum, however, was halted in the 59th minute.
Danijel Milicevic nipped in behind Tottenham's right side and pulled back to Perbet. Davies dived across to block the finish but the ball stuck with the forward, who steered past Lloris at the second attempt.
Spurs pushed for an equaliser, and the all-important away goal, but it could have got even worse had Lloris not palmed Milicevic's shot on to a post in the 76th minute.
It was a night to forget for the visitors.