Nacer Chadli scored from the penalty spot but Federico Bernardeschi's deflected strike in the second half sees the Europa League last-32 tie finely balanced.
Federico Bernardeschi's deflected long-range strike cancelled out Nacer Chadli's earlier penalty as Fiorentina and Tottenham played out a closely fought 1-1 draw in the Europa League on Thursday.
Spurs became the first English team to ever score against the home side in Florence after Ben Davies was fouled inside the area but a big deflection off Ryan Mason saw La Viola draw level.
Fiorentina spurned chances to secure a first-leg lead, with Gonzalo Rodriguez heading narrowly wide at the death, but Mauricio Pochettino will be happy with a valuable away goal ahead of next week's second leg.
A 2-0 defeat in Florence, with goals from Mohamed Salah and Mario Gomez - who have both since left the Serie A club – saw Tottenham defeated 3-1 on aggregate just under a year ago.
Fiorentina, however, had home advantage in the opening leg in the 2015-16 rematch and the club's hopes of winning the tie were boosted by the absence of the injured Hugo Lloris from Tottenham's goal.
Yet replacement goalkeeper Michel Vorm was barely tested in a cagey first half that only came to life in the closing stages.
Mauro Zarate fired a loose ball wide with his left foot after 32 minutes as Tottenham's defense had failed to initially deal with a right-wing cross from Josip Ilicic.
The miss from the former West Ham forward proved costly, as the visiting side broke the deadlock five minutes later.
Left back Davies' slalom run into the area was halted by Nenad Tomovic, with Chadli sending Ciprian Tatarusanu the wrong way with his penalty. In converting from 12 yards out, the Belgium international became the first player from an English team to score at Fiorentina's home ground in UEFA competition.
Tottenham looked to have doubled the advantage within two minutes of the second half getting under way, only for an offside decision to rule out Son Heung-min's stooping header from a Christian Eriksen free kick.
Chadli was then denied by a smart low save by Tatarusanu before Fiorentina equalized with the aid of a rather large slice of luck just before the hour.
Bernardeschi tried his luck from outside the area and hit the jackpot, as his left-footed drive clipped Mason's attempted block and looped over Vorm via a deflection off the underside of the crossbar.
Fiorentina should have gone on to claim the lead in the closing minutes, yet Gonzalo Rodriguez failed to get enough contact with a near-post header from a corner when ideally placed to nod home.
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