Roberto Soldado's best moment in a Tottenham shirt was quickly followed by one to forget as he unnecessarily gave away the free-kick which allowed Fiorentina to secure a draw and what could prove a decisive away goal in this Europa League tie.
This encounter is the first of six vital fixtures Mauricio Pochettino's side face over a testing 17-day period, which includes the mouth-watering prospect of Capital One Cup glory against rivals Chelsea.
The Wembley showdown comes just three days after the return leg of the last-32 tie in Florence - a match they approach off the back of a 1-1 draw at White Hart Lane, where Soldado's moment of magic was cancelled out by a Jose Maria Basanta strike which stemmed from his rush of blood to the head.
The Spaniard was one of six changes made by Pochettino for a match which got off to an ideal start when the £26million striker showed wonderful skill and composure to volley home a Paulinho corner
Spurs looked set to add to that goal during a sustained period of pressure, only for Fiorentina to draw level before half-time as Basanta fired home during a penalty box melee that followed a free-kick Soldado foolishly gave away.
Nacer Chadli saw an effort come off the underside of the bar as Tottenham tried in vain to regain the lead, with not even star turn Harry Kane's second-half introduction able to help them breach the Italian high-fliers' goal.
It was a frustrating end to a match which began so well, with Andros Townsend quickly drawing a foul from Gonzalo Rodriguez, earning the Viola defender a fourth-minute booking.
The resulting free-kick came to nothing but the hosts continued to exert pressure, with only Ciprian Tatarusanu's quick reactions preventing Chadli turning home a defence-splitting Soldado pass.
It saved the Fiorentina backline's blushes, but only for a matter of seconds.
Paulinho's deep corner fell for Soldado to fire an exceptional right-footed volley into the bottom corner - an all too rare flash of the ability which saw Spurs fork out £26million for his services.
While it was an ideal start, Spurs were soon reminded this would be no easy task.
Mario Gomez had two efforts in quick succession before Chelsea loanee Mohamed Salah, the scourge of Tottenham in this competition with Basle two years ago, saw a low shot blocked.
Fiorentina were proving a nuisance in attack but showing signs of defensive frailty, with Christian Eriksen allowed to strike over before Soldado struck an audacious overhead kick at Tatarusanu.
Paulinho and Nabil Bentaleb had efforts of differing quality from distance in between a deflected effort from Townsend, who was threatening to unlock Vincenzo Montella's side down the right.
Spurs were dominating but their failure to capitalise cost them in the 36th minute when Soldado hacked down Joaquin from behind before he could run into the box
It was an attempt at damage limitation which earned a booking and had the opposite effect, as Hugo Lloris saved Matias Fernandez's initial effort, only for the ball to come back off Stefan Savic allowing Basanta to strike home.
Many inside White Hart Lane thought the equaliser - which came shortly after Jan Vertonghen avoided a penalty for bringing down Gomes - was short-lived, although Chadli's effort off the underside of the bar was correctly deemed not to have crossed the line.
Salah curled just wide when the second half of this open and enjoyable match got under way, with Basanta providing a timely block to thwart Eriksen at the other end.
Soldado flicked a header over and Bentaleb struck a hopeful effort over, with Townsend whizzing wide before Kane was introduced in a bid to change the dynamics with 25 minutes remaining.
Gomez bobbed and weaved before lashing over and Paulinho forced a save out of Tatarusanu as play swung from end-to-end, with Soldado getting a header on target from the corner which followed.
Erik Lamela had an attempt and Fiorentina substitute Marcos Alonso sent an effort across the face of goal as both sides pushed for a winner - one which did not arrive despite Fernandez trying his luck in stoppage time.
