Tottenham Hotspur's chances of Champions League qualification took a massive blow after a late equaliser from PSV Eindhoven striker Luuk de Jong earned the Dutch side a draw.
PSV managed to draw level in the final five minutes after the game's momentum swung their way following goalkeeper Hugo Lloris' red card for a reckless foul outside of the 18-yard box.
Harry Kane's header shortly before the hour mark looked to have ensured that Tottenham were heading back to London with all three points. However, former Newcastle striker De Jong's late flick meant more European misery was inflicted on Spurs.
They did not start the game well, falling behind after Toby Alderweireld failed to control a pass which sent winger Hirving Lozano through on goal.
However, the Mexican was very fortunate to see his effort go in. The ball looped over a hapless Hugo Lloris after Alderweireld looked to have atoned for his error with a last-ditch tackle, only for the ball to deflect into the back of the net.
Spurs made it 1-1 shortly before half-time, after some good work by Christian Eriksen saw him find Kieran Tripper on the byline, the England defender pulling the ball back for Brazilian Lucas Moura, whose effort deflected in off a PSV defender.
In the end, they were architects of their own downfall. Lloris' moment of madness ultimately cost his team dearly. Following a free kick, panic ensued in the box, allowing de Jong to finish, leaving Spurs' European dreams in jeopardy.
Key Talking Point
Where do Tottenham go from here? On a night where they simply had to win, a rush of blood to the head of Hugo Lloris meant their hopes of progressing to the knockout stages are extremely slim.
Mere months after a blunder in the World Cup final, Lloris' mistake tonight was far more costly. Spurs had the game in their hands but, in what many people would regard a trademark of this side, they lacked the winning mentality required to come through victorious in big games.
They did have chances to kill the game off against inferior opposition, but lacked a ruthless edge in their attacking play. At this level of football, if you fail to take your chances, you will be punished.
Starting XI: Lloris (2), Trippier (8), Alderweireld (5) , Sanchez (7), Davies (6), Dier (5), Dembele (5), Eriksen (8*), Lucas (6), Son (6), Kane (7).
Substitutes: Lamela (6), Winks (6), Vorm (5)
STAR MAN - This is a rather difficult choice to have to make, given that Tottenham collectively disappeared for the final quarter of the game. If there is one player who stood out, it was Christian Eriksen, back in the side after a month out through injury.
WORST PLAYER - On another day, skipper Lloris could have cost his team all three points. His rating here comes as a result of the jeopardy he put his team in during the game's closing stages. A rash decision from a player who has had an up and down year despite being crowned a World Cup winner.
Tottenham will be massively deflated after a frustrating draw in Holland. However, they have little time to rest on their laurels. They take on Manchester City in their next fixture on Monday night and a win would see them leapfrog the current English champions in the Premier League table.