It ended all-square in Florence so our Europa League Round of 32 tie against Fiorentina will be decided at White Hart Lane on Thursday week (February 25).
Nacer Chadli opened the scoring from the penalty spot on 37 minutes as we controlled the first half at the Stadio Artemio Franchi on Thursday night.
As expected from a team third in Serie A and with the second-best home record in Italy's top flight, Fiorentina came back in the second half and levelled as a touch of fortune went against us and Federico Bernardeschi's 30-yard shot deflected off Ryan Mason before looping home.
Mauricio Pochettino made six changes from the team that was victorious over Manchester City in the Premier League on Sunday.
Michel Vorm came in for the injured Hugo Lloris between the sticks whilst in front of him Kieran Trippier and Ben Davies replaced Kyle Walker and Danny Rose respectively in the full-back slots.
Mason wore the armband in his first appearance since November 29 with Tom Carroll alongside him at the base of the midfield. Chadli started up front, with the three players behind him unchanged from the Etihad - Dele Alli, Christian Eriksen and Heung-Min Son.
It was a quiet opening period from both teams with the first shot on goal in the 18th minute when former Bolton full-back Marcos Alonso blazed an effort over from outside the box.
Our first decent effort on goal came in the 26th minute when Eriksen was given space and let fly from 30 yards with a shot that forced Ciprian Tatarusanu into a smart save.
We had an escape on the half-hour mark when Mauro Zarate missed a Josip Ilicic cross with the ball dropping kindly for Bernardeschi but he shinned it wide from inside the six-yard box.
We had focused most of our attacking play down the left and got a reward in the 37th minute when Carroll linked well with Davies before the Welsh defender was upended by Nenad Tomovic and referee Mr Zwayer pointed to the spot.
Chadli stepped up and coolly rolled the ball to the goalkeeper’s right to break the deadlock.
The home side might have been level in the dying moments of the first half but Zarate fired over after good work on the right hand side.
Mousa Dembele was introduced at half-time in place of Carroll and we were almost off to a flyer in the second half as Son stooped to head home an Eriksen free-kick but he had strayed offside and it was chalked off.
Nine minutes later and we had another great opening when Dembele did brilliantly to feed Chadli who raced through but was denied by a smart low save after cutting back onto his right foot.
Son lashed an effort wide shortly after as we enjoyed our most dominant spell of the game.
From nowhere though the home side found a leveller when Bernardeschi hit one from distance that took a wicked deflection off of Mason and dipped over Vorm's outstretched arm into the top corner.
The goal swung the momentum sharply in the home side’s favour. Harry Kane entered the action with just over 20 minutes to go as we appeared to weather the storm, though the game remained finely poised. Eric Dier soon followed for Chadli.
Fiorentina enjoyed possession at this point but we stood firm defensively and as the game entered the final two minutes, we carved out the next best chance as Alli met Trippier's cross with a spectacular volley that sailed just over.
La Viola almost had the final word, though, a minute later. Vorm had to be sharp down to his left to palm away Zarate's shot and from Borja Valero's corner, Gonzalo Rodriguez glanced across goal from the near post, his header just evading both Matias Vecino and Nikola Kalinic lurking at the far upright.
That was the last of the action and it's fair to say, after our performance in the first hour, a draw was the least we deserved.
Fiorentina (4-2-3-1): Tatarusanu; Tomovic, Gonzalo Rodriguez (c), Astori, Alonso; Costa (Vecino 67), Borja Valero; Blaszczykowski (Kalinic 62), Ilicic (Badelj 61), Bernardeschi; Zarate. Substitutes (not used): Sepe, Fernandez, Pasqual, Babacar.
Spurs (4-2-3-1): Vorm; Trippier, Alderweireld, Wimmer, Davies; Mason (c), Carroll (Dembele 46); Son (Kane 68), Alli, Eriksen; Chadli (Dier 79). Substitutes (not used): McGee, Rose, Walker, Onomah.
Goals: Fiorentina - Bernardeschi 59; Spurs - Chadli 37 (pen).
Yellow cards: Fiorentina - Astori 20; Spurs - Alli 30, Davies 48, Kane 90+3.
Referee: Felix Zwayer (Germany).
Attendance: To follow...