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Tottenham conceded two injury-time goals as they slumped to a Champions League defeat against Sporting Lisbon.
Spurs had a number of good chances but could not take them and looked on course to earn a point in Portugal.
However, in the 91st minute Paulinho headed in from Pedro Goncalves’ left-wing corner to put the hosts ahead.
It got better for Sporting as another substitute, Arthur Gomes, hit a fine, low strike to make it 2-0 and hand Spurs their first loss of the season.
Before the match, Sporting coach Ruben Amorim said Tottenham have “one of the best attacks in the world” but for the first time in their eight matches this season, Spurs could not find a goal.
Richarlison scored twice in a 2-0 home victory over Marseille last week and the Brazilian had a number of chances to put his side ahead.
In the first half he had a shot blocked by ex-Liverpool defender Sebastian Coates, headed at goalkeeper Antonio Adan and put the ball in the net after rounding Adan, but was judged offside when collecting Harry Kane’s through ball.
Richarlison also had chances in the second half but twice put his efforts just wide.
Tottenham, third in the Premier League, dominated the start of the second half against their hosts, seventh in the Portuguese Primeira Liga.
Emerson Royal twice had shots saved by Adan, who also made an excellent stop at full stretch to parry Kane’s powerful angled strike. Ivan Perisic also headed just wide and produced an excellent low cross which Kane was just unable to get on the end of.