Tottenham exited the Carabao Cup at the hands of fourth-tier Colchester United after losing 4-3 in a penalty shootout on Tuesday night following a 0-0 draw in regulation time.
Christian Eriksen saw his spot kick saved and Lucas Moura struck the crossbar in the shootout for Spurs, who have won only two of their eight games in all competitions this season.
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Tom Lapslie then sent Colchester into the last 16 for the first time in 44 years by scoring the decisive penalty past Paulo Gazzaniga. The League Two side are 71 places below Tottenham in the English football pyramid.
Following the match, Spurs boss Mauricio Pochettino said: "Colchester made a fantastic game, it was difficult. We are so disappointed we could not score in 90 minutes. We wanted to go further but we are out."
The result marks the second time in a row that Colchester had beaten a Premier League side in a shootout after taking down Crystal Palace on penalties in the second round.
Pochettino added: "They beat Palace on penalties too, that can happen. That's the beauty of the competition, always something can happen."
Prior to this match, Pochettino had progressed from 21 of his 22 domestic cup ties against sides from outside the top flight, including all 18 he has faced in England.