A youthful Tottenham Hotspur side has been defeated by Portuguese club, Pacos de Ferreira, in the first leg of the Europa Conference League play-off.
Lucas Silva scored the only goal of the match on Thursday night to give Pacos de Ferreira all three points.
The first leg was played in Portugal and the return leg is scheduled for England.
The result in Portugal marked the first defeat for Nuno Espirito Santo as Tottenham head coach.
Tottenham made 11 changes from the team that beat Man City in their Premier League opener on Sunday.
Nuno Espirito Santo gave full debuts to new signings Pierluigi Gollini, Cristian Romero and Bryan Gil, during the match in Portugal.
The return leg will be played in London on Thursday, August 26, 2021.