Tottenham are out of the Europa League after a 2-2 draw against Gent at Wembley.
Spurs had slumped to a 1-0 defeat in Belgium during the first leg, meaning Mauricio Pochettino's team had to settle for a 3-2 aggregate defeat.
Tottenham attacking midfielder Dele Alli was red carded six minutes before half time with the game at 1-1 for a wild challenge.
The England international caught Brecht Dejaegere's leg with the poor challenge and could have no complaints as the referee gave him his marching orders.
Tottenham Hotspur's Dele Alli is sent off during the UEFA Europa League, Round of 32 Second Leg match at Wembley Stadium, London. Picture by Mike Egerton PA Wire/PA Images
By that point, Spurs had already seen Christian Eriksen's 10th minute opener cancelled out by a Harry Kane own goal 10 minutes later.
Despite being reduced to 10 men, Tottenham were able to re-take the lead on the night as Victor Wanyama scored just after the hour.
More: @VictorWanyama strides on to it and curls it superbly into the top left corner from just inside the area. We need another. #COYS
— Tottenham Hotspur (@SpursOfficial) February 23, 2017
But the scorer of the winner for Gent in the first leg, Jeremy Perbet, struck the final blow on 82 minutes to send his side through.
The Belgian club go through to the last-16.
Manchester United sealed their place at that stage of the tournament by completing an aggregate victory over Saint Etienne on Wednesday night.
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