Tottenham had one of the most embarrassing nights in history when the lowest-ranked team in the Europa Conference League lost 2-1 to NS Mura in Maribor, 2-1.
New coach Antonio Conte will have watched with horror as his side lost to a team with a UEFA coefficient ranking of 341 when they died.
Despite being reduced to 10 men just after the half hour when Ryan Sessegnon was sent off, Spurs should still have enough to hold off opponents who lost their last four games in competition and in midfield in the Slovenian league stand .
Instead, they lost to Amadej Marosa’s goal in stoppage time after Harry Kane had previously made up for Tomi Horvat’s shock opening.
Losing means the Spurs will likely have to beat Rennes in their final game to qualify for the knockout stage and they will no longer qualify as group winners, which means they will have to play an extra round.
It was another night of disappointment for those hoping for the chance to impress Conte, with Dele Alli being particularly poor and lasting no more than 52 minutes, and the Italian has more evidence of how great a job is in north London.
The night got off to a difficult start when Tottenham had to endure the problems that are common today on its travels in Europe.
Mura, who was only formed in 2012, pushed into the lead in the 11th minute when Horvat was released on the right. He took advantage of Davinson Sanchez’s slip and flicked inward before rolling his left foot into the far corner.
In Kane, Alli and Tanguy Ndombele, the Spurs had enough individual quality on the pitch to hurt their opponents, but they played without cohesion and inflicted more self-harm on themselves in the 32nd minute.
The whole pre-game story centered on this being Sessegnon’s chance to defend his claim under Conte, but he had a night to forget when he received a second yellow card for an awkward foul against Ziga Kous and was sent off .
Kane almost equalized the 10 men five minutes later after a clean turn, but his shot from 12 yards just missed the target.
In the end, Spurs were lucky enough to come into the break 0-1 deficit when Nik Lorbek shot a shot just wide of the goal while goalkeeper Pierluigi Gollini was rooted to the spot.
Having seen enough early in the second half, Conte introduced Son Heung-min, Lucas Moura, Eric Dier and Ben Davies – and it paid off almost immediately.
Son stormed into the box, circling several defenders before stabbing the palms of Matko Obradovic, who made his first save of the evening.
From the resulting corner, Kane should have equalized, but he steered a free header straight at Obradovic.
Spurs finally equalized in the 72nd minute when Kane delivered a nice finish.
Two Mura defenders left each other a pass from Moura so the English captain could step in in style and come home.
The Spurs pushed for a winner, with Moura trying but they never looked like a win and instead it was the Slovenes who crowned a historic night.
Marosa was released on the right, cutting into Sanchez, and his deflected shot crossed a helpless Gollini to spark wild celebrations.