Premier League side, Tottenham Hotspur have crashed out of the Europa League in the round of 32 after losing 3-2 on aggregate following Thursday's 2-2 second-leg draw against Belgian club Gent at Wembley.
While midfielder, Dele Alli was sent off in the first half, Harry Kane's own goal ensured that Mauricio Pochettino's men failed to reach the quarterfinals of the competition for a fourth consecutive campaign.
Christian Eriksen gave the home side early hope in the 10th minute, levelling the tie with a calm finish past goalkeeper Lovre Kalinic.
But Gent secured a crucial away goal with the help of Kane, who from a corner kick mistakenly headed past his own goalkeeper Hugo Lloris.
And Alli added to Spurs' misery in the 39th minute when he was given a red card for a studs-up kick on Brecht Dejaegere.
Victor Wanyama scored Spurs' second with a shot just inside the box on the hour mark as Tottenham piled on the pressure.
But the visitors finished off the tie in the 82nd minute through second-half substitute Jeremy Perbet, whose deflected shot trickled past Lloris to hand the eighth-placed Belgian side a memorable night at the Wembley Stadium.
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