However, Mauricio Pochettino???s side were let down by two terrible individual defensive errors in the second half at a time when they appeared to be in control of the contest.
The first occurred nine minutes after half-time when Spurs centre-back Federico Fazio gifted the home team possession of the ball on the halfway line, and seconds later experienced striker Mario Gomez raced through to fire Fiorentina ahead.
Then with 19 minutes left to play Jan Vertonghen???s hesitation in the penalty area allowed Mohamed Salah a simple chance that the winger gratefully accepted to end the match as a contest.
Despite knowing they had to score to remain in Europe, Tottenham left 24-goal top-scorer Harry Kane on the substitutes??? bench with Sunday???s Capital One Cup final against Chelsea in mind.
However, the striker???s absence from the starting lineup did not appear to affect the visitors??? performance in the opening 45 minutes as Spurs produced a control display of possession football.
And that should have been rewarded with a crucial away goal just before the half-hour mark when from a Fiorentina corner, Tottenham broke con the counterattack with striker Roberto Soldado played clean through on goal after the Fiorentina offside trap hadf malfunctioned.
But with an unmarked Nacer Chadli alongside him, the Spain international somehow managed to underhit his pass to his team-mate, allowing Fiorentina goalkeeper
Murara Neto to intercept when a goal seemed certain.
And the visitors were made to pay heavily for that miss after the interval when first Fazio passed the ball straight to Milan Badelj, before the midfielder then played Gomez clean through on goal, with the striker making no mistake with a fierce shot past Hugo Lloris.
Meanwhile, it was Vertonghen???s error on 71 minutes that ended any hope the Premier League side may have had of getting back into the game, with the central defender dithering in the box instead of clearing his lines, allowing Salah a simple opportunity from close range with the Egyptian???s third goal in four matches.