A much-changed Tottenham side endured a horror evening in Slovenia as they were embarrassed by NS Mura to leave their hopes of making the Europa Conference League last 16 hanging by a thread.
Amadej Marosa’s injury-time goal sealed a 2-1 result after Harry Kane looked to have salvaged a point for 10-man Spurs.
Kane chipped in after Tommy Horvat opened the scoring and Ryan Sessegnon’s red reduced woeful Spurs’ numbers.
It means a second place in Group G is the best Spurs can hope to achieve.
In their final group game, Spurs host unbeaten Rennes, who have already won the group courtesy of Thursday’s victory over Vitesse Arnhem.
The Dutch side are level on points with Antonio Conte’s side and host Mura in their final match. Both games take place on 9 December.
Finishing second in the group would mean a two-legged play-off for Spurs to reach the last 16, with both games being played in February.
If Spurs’ new Italian boss was under any misapprehension about the size of the task he has on his hands in trying to restore the club’s fortunes, Thursday laid it bare.
They still have a competitive first-choice XI, but on this evidence, those looking to break into it are woefully short of what is needed.
Tanguy Ndombele failed to get any kind of grip on midfield, the defence looked vulnerable even to Mura’s modest frontline and Dele Alli floated tamely through the contest before being replaced in the 54th minute.
Kane was one of two players to keep their starting place from Sunday’s win over Leeds and gave us a glimpse of that famed predatory instinct with his well-taken chipped equaliser but for the rest of the time was a lumbering shell of his former self, full of poor touches and fluffed shots.
It could be argued that Sessegnon was seeking to show eagerness in his first start since late August but it was foolish to lunge in to earn a second booking on the half-hour after he had already seen yellow for hauling a man back earlier in the first half.
The introduction of Son Heung-min, Lucas Moura and Ben Davies early in the second half injected more purpose and threat and it was they that helped build up the momentum for the leveller.
But in pushing for a late winner that would have ensured at least a play-off spot, they over-committed, leaving room for Mura to break and Marosa to find the net via a deflected shot.
They will get another chance to continue this European campaign in two weeks’ time. How many more chances some of these Spurs players will get under Conte remains to be seen.