Tottenham will need a victory in their final Europa Conference League group game and the other result to go their way to reach the knockout stages after they were beaten by NS Mura, the lowest ranked team in the competition.
The rough night began when Tomi Horvat skipped easily around Davinson Sanchez to curl a beautiful strike into the top corner with Spurs looking lethargic in the early stages.
Things took another dire turn for the visitors when Ryan Sessegnon picked up his second yellow card in just the 32nd minute, ending his comeback from injury early and leaving his side with a mountain to climb during an evening which should have been little more than a stroll in the park.
Tottenham did most of the attacking pressing late on but a winner evaded them and instead Mura charged up the field to score with the final kick of the game, Amadej Marosa's effort deflecting past the stranded Pierluigi Gollini.
Rennes drew with Vitesse in Group G's other game but are four points clear in first place. Spurs are third, behind Vitesse in second, and will need the Dutch side to slip up against Mura if they are to reach the next round.
TOTTENHAM PLAYER RATINGS
1. Goalkeeper & defenders
Pierluigi Gollini (GK) - 4/10 - Given no chance by Horvat's bending strike. Came off his line quickly to stop a threatening situation with a header but couldn't get near Mura's winner.
Davinson Sanchez (CB) - 2/10 - Made a right meal of it for the first which saw Tottenham go behind, and deflected the second past Gollini. You know what they say: if you can't cut it on a cold night in Murska Sobota, you won't cut it anywhere.
Joe Rodon (CB) - 6/10 - A decent showing from the Welshman. Won most of his duels and didn't take any chances when his side was in danger.
Japhet Tanganga (CB) - 4/10 - Moved over to right back when Conte made changes before the hour mark, having started in the back three. Will have better days.
2. Wing backs & midfielders
Matt Doherty (RWB) - 4/10 - Pushed high up during the opening stages but couldn't quite get his crosses right when the openings came. Came off before 60 minutes.
Tanguy Ndombele (CM) - 5/10 - Played some nice passes, including one to set up Gil. Brought off for Pierre-Emile Hojbjerg.
Oliver Skipp (CM) - 4/10 - Looked a bit rusty after missing the weekend through suspension. Was late to a few challenges.
Ryan Sessegnon (LWB) - 2/10 - Really talked up the opportunity he was getting before the game. Then he got sent off for two silly challenges with his side 1-0 down. Terrible.
Bryan Gil (RW) - 5/10 - Got in from a nice Ndombele pass but could only swipe high and wide from a tight angle. Looked to dribble when on the ball but didn't get many opportunities after the red card.
Harry Kane (ST) - 6/10 - Struck just wide from a decent opening and headed straight at the goalkeeper from a corner. Took his goal nicely, chipping in from a tight angle.
Dele Alli (LW) - 4/10 - Made some nice runs beyond Kane but his contributions started to dry up as the game went on. Got booked for his role in a scuffle and was subbed off before the hour mark.
Son Heung-min (ST) - 5/10 - Made a quick impact, dribbling wound the Mura defence before seeing a shot saved.
Lucas Moura (RW) - 5/10 - Very erratic and lost the ball whenever he overplayed, but his pass set up Kane to equalise.
Ben Davies (LB) - 3/10 - Came on and gave the ball away which led to Mura's winner.
Eric Dier (CB) - 4/10 - Tried to step up and play threatening passes into midfield but was a bit wasteful.
Pierre-Emile Hojbjerg (CM) - 4/10