Tottenham Hotspur claimed a 1-0 victory over Manchester City, but it came at a great cost as Harry Kane and Dele Alli limped off.
Hueng-min Son drilled home the winner 12 minutes from time after Sergio Aguero saw his first half penalty saved by Hugo Lloris at the Tottenham Hotspur Stadium.
Kane collided with England teammate Fabian Delph and rolled his ankle, while Alli appeared to land awkwardly on his wrist.
The Spurs captain was forced into action after VAR ruled Danny Rose had handled Raheem Sterling̢۪s shot, despite being only a yard away.
And while the penalty save certainly spurred the hosts on, City’s lacklustre performance meant the reigning Premier League champions never looked like they could win the game.
With the return leg taking place in just a weeks time, both sides will need to go back to the drawing board having taken the other’s best punches.
But Spurs may well have to do so without two of their best players at the Etihad.
City were awarded a penalty after 12 minutes when a cross from Mahrez hit Tottenham defender Danny Rose on the arm and referee Bjorn Kuipers pointed to the spot after consulting VAR.
But Aguero’s spot-kick was saved by Hugo Lloris low to his left and the scores remained level.
Tottenham took the lead with 78 minutes gone and it came from Son Heung-min as he regathered the ball after almost running it out.
The Spurs forward ran back around Fabian Delph and curled a shot low past Ederson to put the home side 1-0 ahead.
MOMENT OF THE MATCH
The decision to award Man City’s spot-kick in the first half may not have proved decisive, but it certainly will divide opinion.
According to the letter of the law, Rose’s hand was outside of the ‘silhouette’ of his body and therefore the penalty was the correct decision.
But the distance form the ball and the fact humans need to use their arms to jump suggest justice was somewhat done.
STAR MAN – Heung-min Son
Once again, the South Korean stepped up for his side when they needed him most.
With Kane getting battered by the City defenders at seemingly ever opportunity, Son used his pace and dangerous movement to stretch Pep Guardiola’s side.
It is testament to his diligence that he kept the ball in play for his goal before beating his man to fire home.
City have to keep him quiet if they are to tun this around next week.
MATCH STATS
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