No English side had ever scored away to Fiorentina, so Spurs knew it was never going to be easy. But even in his darkest moments, manager Mauricio Pochettino can't have imagined his team would hand the tie to the Italians with three self-inflicted wounds.
The first an under-hit pass from the hapless Roberto Soldado with the goal at Tottenham's mercy; the second a misplaced pass from Federico Fazio that went straight to Fiorentina; the third a catastrophic lapse of concentration by Jan Vertonghen....
Roberto Soldado's embarrassing mistake was the "key" moment in Tottenham's Europa League exit, but Mauricio Pochettino had no regrets about playing the misfiring striker ahead of Harry Kane.
Having arrived in Florence with the last-32 clash level at 1-1, the Spurs head coach made seven alterations with Sunday's Capital One Cup final against Chelsea in mind.
It was a decision which looked like it would pay dividends after the north Londoners began brightly, yet they petered out at the Stadio Artemio...
Three thoughts from Tottenham's 2-0 defeat and Europa League elimination at the hands of Fiorentina on Thursday night in Italy.
1. Tottenham implode in Florence
Tottenham had more than enough possession and chances over the course of their two matches against Fiorentina to make it through to the last 16 of the Europa League, but glaring errors at both ends of the field proved costly for Mauricio Pochettino's side.
Fiorentina were welcome recipients of gifts from their opponents on a night...