Match ends, Fiorentina 1, Tottenham Hotspur 1.
Tottenham will take an away goal into the second leg of their Europa League last-32 tie with Fiorentina after a draw in Italy.
Spurs took the lead in the first half when Ben Davies was fouled inside the area and Nacer Chadli rolled home the subsequent penalty.
However, Federico Bernardeschi equalised when his deflected strike looped into the net.
Dele Alli shot over late on for Spurs, but a draw was a fair result.
Can Tottenham challenge for three trophies?
Tottenham would be forgiven for prioritising domestic success over European glory this season, given they are in a strong position to challenge for a first league title in 55 years.
They are second in the Premier League, two points behind leaders Leicester, but manager Mauricio Pochettino has expressed a desire to win every competition they are involved in.
Although he made six changes to the side that beat Manchester City on Sunday, there were still several first-teamers involved, including Alli, Christian Eriksen and Chadli.
For large periods of the match they looked like the home side as Fiorentina, perhaps aware of the visitors' threat on the counter-attack, adopted a cautious approach and did not have a shot on target in the first half.
It was not a classic Tottenham display, but the fact a much-changed team was able to secure a positive result away to a team that has won 10 of their 13 home games this season bodes well for Pochettino's ambitions.
Aggressive Alli benefits from patient Pochettino
Pochettino has been widely praised for nurturing Tottenham's young talent, with Alli one of the most exciting to emerge during his tenure.
The 19-year-old once again showed glimpses of the brilliance he is capable of, notably producing a neat bit of skill that almost got him out of trouble when surrounded by four Fiorentina players.
He did, however, show immaturity when he appeared to kick out at defender Nenad Tomovic, and was perhaps lucky to only be booked.
It might have been easy for Pochettino to substitute the midfielder soon after to avoid a potential sending off, but the Argentine instead showed his trust in the youngster by keeping him on.
Pochettino was almost rewarded late on when Alli's spectacular acrobatic effort was just over.
Man of the match - Dele Alli
What they said
Tottenham boss Pochettino, speaking about Alli appearing to kick an opponent: "We need to try to teach him
"He is a young player and he has a lot to learn about elite football.
"It is his first season in the Premier League at Tottenham. He came from League One, he needs to learn a lot. But I didn't see it. Some people say 'yes', say 'no', so I don't know."
The stats you need to know
- Spurs have scored all five of the penalties they've taken in the Europa League (excluding qualifiers), stretching back to November 2011.
- Nacer Chadli was the fifth different scorer of those penalties in the Europa League, following Luka Modric, Jermain Defoe, Roberto Soldado and Andros Townsend previously.
- Four of Chadli's six goals for Spurs this season have been in cup competitions (three in the FA Cup, one in the Europa League).
- Spurs have kept only one clean sheet in their last seven away European games.
- Federico Bernardeschi has scored four goals in six Europa League games this season, including three in his last three.
- Fiorentina are unbeaten in five games against English opposition (W3 D2), the last three of which have been games against Spurs.
The return leg is at White Hart Lane on 25 February. Before then, Spurs host Crystal Palace in the FA Cup on Sunday.
- 13AstoriBooked at 20mins
- 16BlaszczykowskiSubstituted forN Kalinicat 62'minutes
- 6Facundo CostaSubstituted forVecinoat 67'minutes
- 20Valero Iglesias
- 72IlicicSubstituted forBadeljat 61'minutes
- 9N Kalinic
- 33DaviesBooked at 48mins
- 28CarrollSubstituted forDembéléat 45'minutesBooked at 67mins
- 7Son Heung-MinSubstituted forKaneat 68'minutesBooked at 90mins
- 20AlliBooked at 30mins
- 22ChadliSubstituted forDierat 79'minutes
- Felix Zwayer
- Shots on Target
Second Half ends, Fiorentina 1, Tottenham Hotspur 1.
Davide Astori (Fiorentina) wins a free kick in the defensive half.
Foul by Harry Kane (Tottenham Hotspur).
Harry Kane (Tottenham Hotspur) is shown the yellow card.
Foul by Marcos Alonso (Fiorentina).
Mousa Dembélé (Tottenham Hotspur) wins a free kick in the defensive half.
Attempt blocked. Milan Badelj (Fiorentina) right footed shot from outside the box is blocked. Assisted by Marcos Alonso.
Attempt missed. Mauro Zárate (Fiorentina) right footed shot from outside the box is close, but misses to the left.
Attempt missed. Gonzalo Rodríguez (Fiorentina) header from very close range is close, but misses to the left. Assisted by Federico Bernardeschi with a cross following a corner.
Corner, Fiorentina. Conceded by Kevin Wimmer.
Attempt saved. Mauro Zárate (Fiorentina) right footed shot from outside the box is saved in the bottom right corner. Assisted by Borja Valero.
Kieran Trippier (Tottenham Hotspur) wins a free kick in the defensive half.
Foul by Marcos Alonso (Fiorentina).
Attempt missed. Dele Alli (Tottenham Hotspur) right footed shot from the centre of the box is too high. Assisted by Kieran Trippier with a cross.
Offside, Fiorentina. Gonzalo Rodríguez tries a through ball, but Borja Valero is caught offside.
Corner, Fiorentina. Conceded by Kieran Trippier.
Foul by Eric Dier (Tottenham Hotspur).
Borja Valero (Fiorentina) wins a free kick on the left wing.
Corner, Tottenham Hotspur. Conceded by Matias Vecino.