Tottenham suffered a major blow to their Europa League hopes after falling to a 1-0 defeat against AZ Alkmaar in the first leg of their last-16 tie.
A comedy own goal from teenager Lucas Bergvall proved the difference in a flat performance from Ange Postecoglou's side.
The defeat leaves Spurs with work to do in next Thursday's return leg at home as they attempt to rescue their season.
Bergvall's unfortunate moment came when he shinned an attempted clearance from Troy Parrott's cross into his own net.
Lucas Bergvall had a tough time after scoring an own goal
The midfielder sliced at the clearance in his own box, which looped into the top corner of the Tottenham net.
Spurs were fortunate not to fall further behind with goalkeeper Guglielmo Vicario producing a fine save to prevent former Tottenham striker Parrott from doubling the home side's lead.
Postecoglou's side created little of note in a muted display, managing only one shot on target all night.
The visitors' attacking statistics made for grim reading, with just two attempts inside AZ's box throughout the entire match.
Substitute Wilson Odobert provided Tottenham's only late effort on target and also headed over the bar in the closing moments.
The lacklustre performance highlighted Spurs' struggles to break down the Dutch side's defence.
Vicario proved crucial in keeping Tottenham firmly in the tie with three big saves throughout the match.
The Italian goalkeeper's most notable intervention came against former Spurs striker Parrott, who was denied what would have been a second goal for the Dutch side.
Dominic Solanke suffered an injury against AZ
PA
Without Vicario's heroics between the posts, Postecoglou's team could have faced an even steeper challenge for the return leg in London.
To make matters worse for Tottenham, midfielder Rodrigo Bentancur will be suspended for the second leg at home next Thursday.
The Uruguayan received his third booking of the Europa League campaign, ruling him out of the crucial return fixture.
