Ryan Sessegnon received a red card as Tottenham crumbled to a dramatic 2-1 defeat to Mura in the Europa Conference League.
Spurs boss Antonio Conte had hailed the players potential in his pre-match press conference and said he couldnt wait to watch his performance.
However, he received two fair yellow cards in the first half in a sluggish performance which many of his team-mates mirrored. Mura went into half time with a one-goal lead which was fully deserved after their excellent desire and Tottenhams poor showing.
In the second half, Conte made four changes at once and Spurs got back in it. Harry Kaneequalised, but they could not find a winner and Mura instead netted a last-gasp winner. Spurs qualification to the knockout stages therefore remains in question heading into the final game.
Mura were much the better team in the first half. As well as executing their game plan well, Tottenhams sloppy approach helped their cause.
The danger signs for the visitors were there when Tomi Horvat volleyed over the bar inside the first 10 minutes. He drove forward and decided to have a go, but Spurs goalkeeper Pierluigi Gollini watched the ball sail over.
However, Tottenham did not heed the warning. Two minutes later, Horvat opened the scoring.
After receiving a pass on the right flank, he cut inside and easily got past Davinson Sanchez, who slipped. The Slovenian then curled a fine finish into the top corner which gave Gollini no chance.
Spurs tried to get back into the game, but ultimately they were sloppy in attack and defence. Matt Doherty had chances to cross but he was wide of the mark on both occasions. For one effort, Bryan Gil could not sort his feet out, with the ball just behind him.
But when the 20-year-old found himself in a better position, he could only blaze over. Meanwhile, Kane shot wide and Dele Allis passing was poor.
To make matters worse, Sessegnon then got a red card. Having already received a yellow, he lunged into a needless challenge on the touchline in Muras half.
Kane equalises, but Tottenham lose
Son Heung-min was one of the four players who came on for Spurs at half time. He came closest in Tottenhams first chance of the second half. He had an effort saved as there was a marked increase in intensity from the visitors.
However, it was Kane who got Spurs level. Lucas Moura, who replaced Doherty, fed the England captain with a great pass and he chipped the ball across the goal and into the side of the net.
Kane had another chance from a corner, but he was denied at the back post.
But as Spurs kept fighting to find a winner, Mura went up the other end and Amadej Marosa netted the winner in stoppage time. Like in the first half, Sanchez got caught out as his opponent cut inside and Marosas shot deflected over Gollini.
As a result, Spurs fell to defeat in a match they will feel they should have won. For Mura, though, it is a feather in the cap for coach Ante Simundza.
The loss leaves Tottenham third in Group G heading into the final match day.