Dinamo Zagreb stunned Tottenham Hotspur in the Europa League as Mislav Orsic scored a hat-trick to send the Croatian side into the quarterfinals of the competition.
The Croatian champions progressed 3-2 on aggregate.
Orsic put the hosts ahead on the night after 62 minutes, before netting again in the 82nd.
The winger rounded off a spectacular night for the hosts by scoring the winner in the 106th minute. Spurs have now lost two games in a row following the North London Derby defeat at the weekend.
Jose Mourinho now faces mounting pressure as questions around his role as manager are raised.
Story of the game
Spurs had made seven changes from the timid squad that started against Arsenal at the Emirates on Sunday.
Harry Kane, Lucas Moura, Davinson Sanchez, and Hugo Lloris were the chosen four that retained their places ahead of the crunch tie on Thursday evening.
There was no Pierre-Emile Hojbjerg due to a suspension picked up in the reverse fixture for the visitors. Mourinho recalled the same back-four that started against Zagreb in London a week ago.
Eric Dier, Ben Davies and Serge Aurier came in for those that featured in the North London Derby. Erik Lamela provided some attacking intent for the side, despite being sent-off for Spurs at the weekend.
Zagreb made only made one change to the side that fell to a 0-2 defeat in London, with Bartol Franjic filling in for Marin Leovac at left-back.
The first 20 minutes of the match played out passively from both clubs. Spurs dominated possession, but never really progressed into any dangerous positions in the Zagreb half.
The first chance of the game came through Orsic, who had a long-range effort comfortably saved by Lloris. At the other end of the pitch, Kane played a teasing ball across the face of the six-yard box, but there were no yellow shirts on the end of it.
It was evident that Spurs were going through the motions, with plenty of punts up the pitch and misplaced passes during the first half.
The game eventually livened up around the half-hour mark.
The Spurs back-line were caught napping as Lovro Majer advanced into the opposition box, before slicing a right-footed shot just wide of the Spurs goal.
Moments later, Majer was looking dangerous again.
The Zagreb-born talisman attempted a delicious ball in between the two Spurs centre-backs, before Sanchez stuck out a foot to prevent the hosts from being in on goal.
The Croatian champions came close again as Orsic had an attempt blocked by Sanchez from outside the box.
Spurs managed to regain their control of the game in the closing stages of the first half. Kane and Lucas combined, with the latter slipping Kane in on goal before the England captain saw his effort saved by Dominik Livakovic.
The half-time whistle sounded not a few minutes later, with Spurs still two-up on aggregate, but with much room for improvement. 0-0 was a fair reflection of the first-half, as chances were few and far between in a less than thrilling Europa League tie.
With no changes made by either camp at the break, there was a worry that the game would fall back into the pattern it had in the opening 45 minutes.
Zagreb certainly came out on the front foot, looking to reduce the deficit already inflicted upon them. Majer was involved again, looking for his tenth assist of the season. He played a delicate pass-in for Bruno Petkovic who had his effort blocked on the edge of the box - a common theme in this match.
Spurs were clearly coasting through this one, as their attitude seemed to replicate that of the first-half. A lack of willingness to get forward from Davies and Aurier had meant that Dele Alli was finding it difficult to get involved.
Gareth Bale was introduced in place of Lamela on the 60-minute mark to try and inject a bit more life into the game, having been withdraw early into the second half against Arsenal.
Spurs got what they deserved a few minutes later.
Majer played in Orsic down the left-hand side, who cut back across the retreating Aurier, before curling a magnificent shot into the top right-hand corner.
Lloris was helpless as the left-winger netted his 16th goal of the season, in all competitions.
This goal epitomised yet another horrific Spurs outing. Mourinho, having seen enough, introduced Tanguy Ndombele, and Giovani Lo Celso not long after.
This was Lo Celso's first game since December, having picked up a hamstring injury at the end of 2020.
The Argentine seemed fired up upon his return, as he forced an early save from Livakovic. This was Spurs' second shot on target of the entire evening.
As the game entered the final ten minutes of the match, Spurs still found themselves on the back-foot.
They were seemingly stuck between trying to get a goal, and sitting on their lead, a gamble that had rarely paid off for the North London club this season.
History repeated itself not long after. Iyayi Atiemwen ventured forward into the Spurs final third, before pulling a cross back in the hope of a Zagreb player being on the end of it.
Atiemwen found his man, as Orsic fired in his second of the night, drawing Zagreb level on aggregate, and 2-0 up on the night.
It was no more than Spurs deserved, who were putting on a performance to rival what occurred in London at the weekend.
Kane had the only real remaining chance for Spurs, but his header was kept out late on.
Extra-time loomed, Carlos Vinicius and Sergio Reguilon were summoned by Mourinho, whilst Petar Stojanovic and Josip Misic were introduced for Zagreb.
Spurs had the best chances of the first half of extra-time, although poor positioning from Dier and Reguilon almost resulted in the hosts scoring a third.
Bale fizzed a low shot just wide of the post, a goal that could well have put this tie out of sight for Zagreb.
Vinicius had shot blocked after Reguilon pulled a cross across the box before the half-time of extra-time whistle went.
Catastrophe struck just a minute into the final quarter of an hour. Orsic, ventured into a darting run, weaving in and out of almost the entirety of the Spurs and midfield and defence before burying a powerful shot past Lloris' front post.
There was a flurry of massive chances for Spurs with five minutes remaining, as Kane and Bale all had efforts cleared off of the line.
However, it was not enough for Spurs, Zagreb held on to their lead, knocking Spurs out of the Europa League, and piling all of their hopes of a trophy into a seemingly impossible tie against Manchester City in April.
Same old Spurs
This was arguably Spurs' worst performance of the season.
They had the tie in their hands at the start of the night but, a sheer refusal to put any kind of effort into the game, resulted in Zagreb deservedly progressing.
Mourinho will be sweating at the level of backlash he will receive after this game. The Portuguese manager was seemingly throwing all of his eggs into one basket, but they have all cracked.
Kane looked to be playing at 50%, no Heung-Min Son, and another no-show from Dele was the biggest problem for Spurs tonight. Continuously, there was a lack of urgency that fans will all too familiar with in Croatia tonight.
There seemed to be no passion, no skill and no quality.
Credit where it is due, Zagreb were excellent. They came into the match with a game plan and executed it superbly. Orsic was the standout player, and he demonstrated everything Spurs fans will wish they had seen from their recruits.
Is this the end for Mourinho?
Many were sceptical about Mourinho going into this game, and this result will have been the final straw.
Spurs are yet to beat a top-half side in 2021, and crashing out of this competition will have put question marks over the future of who the manager of the club is.
It certainly is strenuous times for Daniel Levy, who clearly appointed Mourinho for the sole purpose of winning silverware.
Spurs are a side that continues to decline, and you have to question whether an entire rebuild is needed next season if they are going to reach the levels they had originally under Mauricio Pochettino.