Tottenham exited the Europa League after an error-strewn 2-0 defeat by Fiorentina gave the Italian side a 3-1 aggregate win.
Mario Gomez raced clear after a second-half mistake by Federico Fazio and slid the ball under Hugo Lloris.
Chelsea loanee Mohamed Salah sealed the win after a blunder by Jan Vertonghen.
Spurs needed to score in Florence, but were unable to make a breakthrough, with striker Roberto Soldado wasting a golden first-half opportunity.
The Spanish striker was played clean through by Erik Lamela’s swept pass after Spurs broke quickly from a corner, but he scuffed his attempt to square the ball to Nacer Chadli and keeper Neto gathered.
The result is a blow for Spurs before their biggest game of the season so far – the League Cup final against Chelsea on Sunday.