Kevin Kampl's second-half goal condemed Tottenham Hotspur to another Champions League defeat at Wembley, handing Bayer Leverkusen a 1-0 away win as the Lilywhites were left in a difficult position from which to qualify for the knockout round.
Spurs never got going throughout the game in a poor performance, and you couldn't say that they deserved to get anything from the game, Kampl securing all three points for Bayer with a cool finish past Hugo Lloris on the 65 minute mark.
Spurs never start as Kane remains sidelined
The home fans were left disappointed even before the game as Harry Kane failed to make the squad, despite suggestions earlier in the week making out that he had a good chance of taking his place on the bench.
With Son Heung-Min preferred to Vincent Janssen as the lone striker, the South Korean struggled to make an early impact as Spurs' started sloppily, Jan Vertonghen spooning a clearance into Javier Hernandez's path, Hugo Lloris lucky not to face an early shot on his goal.
£30million man Moussa Sissoko was picked to start from the right wing, yet proved a constant source of frustration in the early stages, often getting the better of left-back Wendell only for his final product to be poor.
Mauricio Pochettino was forced into a change just after the hour mark, with Dembele hobbling off for Janssen, Christian Eriksen dropping deeper and Son moving out to the left. It was Eriksen who registered Spurs' first shot on target, a powerful effort beaten away by Bernd Leno.
Tottenham almost went behind just before the break, a costly error from Kyle Walker allowing Brandt room in the area, Vertonghen coming in to deny him a goal with a perfectly-timed challenge.
Penalty shout waved away
The hosts did start the second half in more positive fashion, and felt that they should have been awarded a penalty when Dele Alli was tripped by Toprak inside the penalty area, to no avail. Eriksen picked the ball up from that incident and got a shot away, his strike flashing wide.
However, defensive errors began to creep back in as a comfortable Leveruksen side looked to flex their muscles going forward. A poor defensive header from Eric Dier left Hernandez in space to shoot in the area, Vertonghen sliding in brilliantly to tackle before the Mexican had another attempt saved on the line by Lloris.
Kampl bags winner
That was a warning sign that Spurs didn't react to, Kampl opening the scoring less than five minutes later. The Tottenham defence allowed the ball to be played around in front of them, before Aranguiz's deflected effort found Kampl in-behind the defence, the midfielder cooly giving Lloris the eyes and slotting home.
If you thought that goal would spark a response from Tottenham, you'd have been wrong, as it took 20 minutes for them to show any signs of striking back, Dier striking the bar with a nicely executed free-kick.
However, if that set-piece had gone in it wouldn't have been a deserved equaliser, as Spurs were deserving of what they got - nothing.
Now they must go to group leaders Monaco and pray for victory, or face being knocked out with a game to spare. Bayer can qualify for the last 16 by beating CSKA next time out, and hoping Tottenham drop points in France.