Tottenham Hotspur took on Sporting Lisbon in a Champions League crunch match for Antonio Conte's Lilywhites.
Conte made six changes to the side that lost to Newcastle United on Sunday with welcome returns for Cristian Romero and Pierre Emile Hojbjerg
Tottenham began the night top of Group D on seven points but were only separated to the bottom of the group Eintracht Frankfurt by three points.
Story of the match
After a cagey opening 12 minutes, it was Sporting who went closest as a Sebastian Coates header went narrowly wide of the post from a corner.
This appeared to give Tottenham the wake-up call they needed. Harry Kane forced an awkward save from Sporting keeper Antonio Adan just five minutes later following a string of half chances.
Paulinho gave Tottenham another warning on 20 minutes as he fired just over the crossbar from ten yards out from a sumptuous cross from Pedro Porro.
Tottenham failed to pick up on these warning signs and after 22 minutes Tottenham academy graduate, Marcus Edwards, put the Lisbon side 1-0 up against his former club.
Edwards picked up the ball halfway inside the Spurs half and skipped past the desperate challenges of Eric Dier and Pierre Emile Hojbjerg before rolling a shot back across goal and past an outstretched Hugo Lloris.
The North London side still failed to pick up the initiative and looked disjointed and lethargic after going a goal down.
Shortly after this, Sporting had the ball in the Tottenham net again. Fortunately for Spurs, Sebastian Coates was found to have handled the ball into the net.
While the goal was clearly disallowed, there was a palpable sense of disbelief around the ground at how easy Sporting were finding it to hurt Tottenham.
In added time of the first half, Harry Kane won a freekick 30-yards out and gave his side a serious chance to attack the Sporting Lisbon goal.
Hojbjerg stood over the ball in a dangerous crossing position. The Dane rolled the ball to Rodrigo Bentancur in what can only be assumed to be a set-piece routine.
Bentancur then played the ball across the box to Son who proceeded to slip and fall. If ever there was a ten-second summary of Tottenham's first half, that was it.
Five minutes into the second half Tottenham finally produced a dangerous counterattack. A dangerous Hojbjerg cross was palmed inches away from the onrushing Harry Kane.
Antonio Conte's men continued to look the stronger of the two sides in the second half and were beginning to sustain pressure on Sporting Lisbon.
Matt Doherty produced a fine save from Adan on the half-volley as a cross sailed over to him. Adan got down well with a strong arm to deny the Irishman.
Eric Dier then headed narrowly over the bar with 15 minutes to go from a dangerous corner. Tottenham were getting closer.
Sporting reminded Tottenham that they were still dangerous on the counterattack.
The Portuguese side had two huge misses in as many minutes. The first a smart Lloris save, the second an off-target, open-goal sitter.
Then finally, finally, Tottenham got their goal. A towering header from Rodrigo Bentancur in the 80th minute, beating the Sporting keeper, Adan to the corner kick.
Dier then had the chance to put the home side a goal up, another header glanced inches wide from a superb Son cross.
And then, in quite literally the dying embers of the five additional minutes played of the game, a deep cross from Ivan Perisic found Emerson Royal at the back post.
He headed to Harry Kane who smashed the ball into the back of the net from no more than 6 yards out.
Tottenham had snatched back victory and a place in the round of 16.
Or so they thought, after a four-minute VAR check, the officials disallowed the goal. The air was audibly sucked out of the Tottenham Hotspur Stadium.
Amidst the outcry from Tottenham's players and coaches at the decision, Antonio Conte was sent off for his protests.
Player of the match: Sebastian Coates
By no means the glamourous choice, and honourable mentions must be given to Marcus Edwards and Rodrigo Bentancur, but Coates embodied everything that the Sporting performance was about.
Calm and composed on the ball, brave and aggressive without it. Coates played a fantastic, line-breaking pass to Edwards for his side's goal.
The experienced centre half was winning everything in the air and remained unflustered on the ball, even in the tense latter stages of the match.
The entirety of group D are now separated by just two points. Tottenham remain top on eight points but they must now travel to Marseille in the final group game.
Conte's men will have to at least match Eintracht Frankfurt's result against Sporting to progress to the round of 16.