Tottenham somehow strived to chuck away a 2-0 first-leg lead to crash out of the Europa League in the round of 16 after falling to a lame 3-0 defeat after extra time to Dinamo Zagreb.
With what looked a solid lead from the first leg, Jose Mourinho named a strong side for what he hoped would result in routine progress.
Zagreb’s preparations for the game were thrown into disarray when their coach was jailed for fraud.
However, Mislav Orsic’s two second half goals took the tie to extra time with the hosts good value for the result.
But the best was yet to come when, in the second half of extra-time, Orsic hit a winner of stunning quality. Picking the ball up 40 yards from goal, he ran at the Spurs defence and fired a great strike into the corner of Lloris’ net.
The goal sparked crazy scenes at the Stadion Maksimir as Orsic wrote his name into Dinamo folklore.
Zagreb made a strong start at the and were clearly not ready to wave the white flag, despite being 2-0 down from the first leg.
Despite their making all the early running though, Hugo Lloris’ goal remained largely untroubled.
Indeed, the first meaningful chance fell to Erik Lamela after 27 minutes when he found himself in space. However, the Argentine took too long to get his shot away and the chance was blocked.
Tottenham though survived a big scare 11 minutes before the break. That’s after the ball fell kindly to Lovro Majer in the centre of goal. However, he fluffed his lines and dragged his shot wide of goal.
Moments later, Lloris had to be alert to push away another effort on his goal.
Spurs, however, finished the half the stronger with Serge Aurier steering a header over. Kane then had his first sight at goal only to see his effort from a tight angle blocked as the sides went in goalless.
Zagreb again made a strong start to the second half, a free header from Arijan Ademi gleefully collected by Lloris.
Spurs introduced Gareth Bale on the hour mark to breathe new life into their attack, with the ineffective Lamela making way.
However, it was Dinamo who took the lead two minutes later when Orsic scored a stunning goal. Picking up the ball on the edge of the area, the Croatian took a touch inside Aurier and curled an unstoppable 20-yard effort into the top corner.
That was the cue for a period of sustained pressure from Zagreb.
Zagreb score two second-half goals
Spurs introduced Giovani Lo Celso in place of Dele Alli; the Argentine making his first appearance since December 20 after a hamstring problem. He came on alongside Tanguy Ndombele, with Harry Winks also making way.
Lo Celso was quickly in on the action, his deflected shot producing a smart save Domink Livakovic.
However, that was a rare sighting on goal and Zagreb grabbed a deserved leveller on 84 through that man Orsic again.
After the ball was crossed the right, he was the man in the right place to rattle a 12-yard strike past Lloris.
That seemed to spring Spurs into life, with Kane seeing a header from a tight angle cleared off the line.
Spurs finished regular time the stronger as Zagreb sat in, but there was no way through as the match entered extra time.
But it was the hosts who continued to ask questions in the first period of added-on time.
Indeed, Marin Leovac found himself through on goal from a narrow angle. However, he produced neither a meaningful shot or a cross as the ball trickled just wide.
Bale then fizzed a low, 25-yard drive just wide, while substitute Vinicius began to impose himself on the Zagreb defence.
However, Orsic scored a stunning third to spark absolute jubilation for the hosts.
The job was not done though with that being the cue for some solid Spurs pressure.
Spurs did manage to carve out some good openings with Kane and Bale going close. But truth be told it was too little too late with Zagreb deservedly progressing.
The result will come as a crushing blow for Mourinho who will now face more questions on his future after the tame exit.