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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.
Spurs left to wonder what might have been
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.
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Sporting Lisbon
Squad number1Player nameAdán
Squad number25Player nameGonçalo Inácio
Squad number4Player nameCoates
Squad number2Player nameMatheus Reis
Squad number24Player namePorro
Squad number15Player nameUgarte
Squad number5Player nameMorita
Squad number11Player nameNuno Santos
Squad number17Player nameTrincão
Squad number10Player nameEdwards
Squad number28Player namePote
Squad number6Player nameAlexandropoulos
Squad number20Player namePaulinho
Squad number33Player nameArthur Gomes
Squad number47Player nameRicardo Esgaio
Tottenham Hotspur
Squad number1Player nameLloris
Squad number17Player nameRomero
Squad number15Player nameDier
Squad number33Player nameDavies
Squad number12Player nameEmerson Royal
Squad number5Player nameHøjbjerg
Squad number30Player nameBentancur
Squad number14Player namePerisic
Squad number9Player nameRicharlison
Squad number7Player nameSon Heung-Min
Squad number10Player nameKane
Squad number21Player nameKulusevski
Line-ups
Sporting
Formation 3-4-3
- 1Adán
- 25Inácio
- 4Coates
- 2Reis de LimaBooked at 75mins
- 24Porro
- 15Ugarte
- 5MoritaBooked at 63minsSubstituted forAlexandropoulosat 71'minutes
- 11Gomes dos SantosSubstituted forde Sousa Esgaioat 90+2'minutes
- 17Machado TrincãoSubstituted forDias Fernandesat 76'minutes
- 10EdwardsSubstituted forGomes Lourençoat 90+2'minutes
- 28Pereira Gonçalves
Substitutes
- 6Alexandropoulos
- 12Israel
- 16Costa Rocha
- 18Fatawu
- 20Dias Fernandes
- 22Eusébio Paulo
- 33Gomes Lourenço
- 47de Sousa Esgaio
- 63Martinez Marsà
- 71Basilua Jacinto Názinho
Tottenham
Formation 3-4-2-1
- 1Lloris
- 17Romero
- 15Dier
- 33Davies
- 12Emerson RoyalBooked at 81mins
- 5HøjbjergBooked at 84mins
- 30BentancurBooked at 61mins
- 14Perisic
- 9Richarlison
- 7Son Heung-MinSubstituted forKulusevskiat 72'minutes
- 10Kane
Substitutes
- 2Doherty
- 4Skipp
- 6D Sánchez
- 11Gil
- 19R Sessegnon
- 20Forster
- 21Kulusevski
- 24Spence
- 25Tanganga
- 34Lenglet
- 38Bissouma
- 42White
Referee:Srdjan Jovanovic
Attendance:39,899
Live Text
Match ends, Sporting Lisbon 2, Tottenham Hotspur 0.
Second Half ends, Sporting Lisbon 2, Tottenham Hotspur 0.
Goal! Sporting Lisbon 2, Tottenham Hotspur 0. Arthur Gomes (Sporting Lisbon) right footed shot from the left side of the six yard box to the centre of the goal. Assisted by Paulinho.
Substitution, Sporting Lisbon. Ricardo Esgaio replaces Nuno Santos.
Substitution, Sporting Lisbon. Arthur Gomes replaces Marcus Edwards.
Goal! Sporting Lisbon 1, Tottenham Hotspur 0. Paulinho (Sporting Lisbon) header from the left side of the six yard box to the top right corner. Assisted by Pote with a cross following a corner.
Corner, Sporting Lisbon. Conceded by Hugo Lloris.
Attempt saved. Pedro Porro (Sporting Lisbon) left footed shot from outside the box is saved in the bottom left corner.
Foul by Pote (Sporting Lisbon).
Emerson Royal (Tottenham Hotspur) wins a free kick in the attacking half.
Pierre-Emile Højbjerg (Tottenham Hotspur) is shown the yellow card for a bad foul.
Manuel Ugarte (Sporting Lisbon) wins a free kick in the attacking half.
Foul by Pierre-Emile Højbjerg (Tottenham Hotspur).
Attempt blocked. Nuno Santos (Sporting Lisbon) left footed shot from outside the box is blocked.
Corner, Sporting Lisbon. Conceded by Ivan Perisic.
Emerson Royal (Tottenham Hotspur) is shown the yellow card for a bad foul.
Nuno Santos (Sporting Lisbon) wins a free kick in the defensive half.
Foul by Emerson Royal (Tottenham Hotspur).
Offside, Tottenham Hotspur. Dejan Kulusevski tries a through ball, but Emerson Royal is caught offside.
Paulinho (Sporting Lisbon) wins a free kick in the attacking half.