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 guilty of wasting the best opportunity.
You can watch the highlights of the match here
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