A comical own goal from Lucas Bergvall in the first half of the match was the reason for Tottenham's failure, who lost 0-1 away to AZ Alkmaar in the first leg of the 1/8 finals of the Europa League.
Bergwall cleared Troy Parrott's shot on 18 minutes and it was enough to give AZ their first win over the English side in 12 attempts.
Spurs had eight days to prepare for the encounter but were unimpressive in the Netherlands and failed to register a shot on target until the 88th minute.
It was a hugely disappointing performance from Ange Postecoglou's side, especially considering that this tournament remains the club's last hope for a trophy this season and the only way to salvage a difficult campaign.
Tottenham will now need to put in all their efforts ahead of Thursday's return leg in north London.
Postecoglou resisted the temptation to field the returning trio of Micky van de Ven, Christian Romero and Dominic Solanke and injuries did hit the hosts when Michael Lahdo was forced off after just eight minutes at the AFAS Stadium.
This contributed to a sluggish start to the game, but AZ, given their first real chance of the match, somehow took the lead in the 18th minute.
A Peer Koopmeiners corner fell to former Spurs striker Parrott, who fired on target but Bergwall made a poor clearance and watched in horror as his effort flew over Jed Spence and into the net.
It was an awkward own goal and although Tottenham tried to respond, Parrott was soon in the spotlight again as Archie Gray blocked his shot and then Ernest Poku sent the ball wide.
An even better opportunity came in the 31st minute when AZ broke ahead after a chance by Son Heung-min and Parrott received the pass but Guglielmo Vicario ran forward and made a superb save from the Republic of Ireland forward.
Son's poorly taken short free-kick ended the first half for Spurs before the visitors survived a goalmouth scramble when James Maddison slid forward to deny David Moller Wolff and Bergwall blocked Kopmeiners' effort.
The score remained 1-0 at the break but Postecoglou responded by replacing Matis Tela with Wilson Odobert and Tottenham increased the pressure, Bergwall firing wide before Son fired over the bar.
AZ continued to pose a threat and Poku forced Vicario into another save from Moller Wolf's dangerous cross.
Sourse: breakingnews.ie
