Can former West Brom and Fulham men shatter Spurs' European dream?
When they step out at White Hart Lane on Thursday evening, there will be a feeling of familiarity that stretches beyond the famous Fiorentina shirt once worn by the likes of Roberto Baggio, Gabriel Batistuta and Manuel Rui Costa.
As well as Micah Richards, the likes of Alberto Aquilani, Marcos Alonso, David Pizarro, Stefan Savic and Mohamed Salah have all previously played for English clubs, while manager Vincenzo Montella spent six months on loan at Fulham back in 2007. The first of his two Premier League goals came against Spurs.
The coach was well-liked at Craven Cottage, and has quickly won admirers in Florence for the work he has done in turning around the Viola's fortunes since his appointment in June 2012.
Passed over by Roma after a successful stint as an interim coach during the final three months of 2010/11, Montella spent time learning his craft at Catania, arriving at the Stadio Artemio Franchi far more experienced and well-rounded.
Cesare Prandelli was a tough act to follow, having steered the club to a Europa League semi-final they lost on penalties to Rangers, then to the knockout stages of the Champions League in 2010.
In doing so, his team recorded home and away victories over Liverpool, inspired by the performances of a young Stevan Jovetic. The Montenegrin was one of few players to remain during the summer that Montella was appointed, as Fiorentina signed a staggering 17 new faces in a complete rebuild of the side.
After helping the new coach to a fourth-place finish, Jovetic moved to Manchester City, with the club hoping Mario Gomez and Giuseppe Rossi could score the goals needed in order to compete for trophies.
Yet the pair were rarely fit enough to take to the field together, and Juan Cuadrado instead became the star attraction as they once again ended the campaign just outside the Champions League positions.
The current season got off to a poor start as, still without Gomez and Rossi, they won just three of their opening 11 games and slid into the bottom half of the table.
That run culminated with a home defeat against Napoli, after which sporting director Daniele Prade backed his coach to stem the flow of bad results, while owner Andrea Della Valle spoke of the players being under too much pressure to perform. It was a much happier dressing room the following week; victory over Hellas Verona kick-started Fiorentina’s season, and they have lost just once in their 12 league matches since.
The Viola look back to their best once again – in fact, only two teams on the peninsula have conceded fewer goals than the 23 Montella's men have shipped this term.
They play football that's easy on the eye, based on short passes and quick movement, with only nine sides in Europe’s top five leagues able to better their 58% average possession rate.
Having previously scored just once this term, Gomez has netted five goals in his last four appearances. He will be well rested on Thursday too, sitting out Fiorentina’s win over Sassuolo as ex-Chelsea star Salah turned in an impressive performance, notching a goal and an assist on his first start for the club.
Also in that game, however, a late goal for their opponents highlighted a feeling that Fiorentina's defence has flaws which can be exposed. Indeed, since the nine games where Neto was replaced in goal by Ciprian Tatarusanu, Fiorentina have conceded 11 goals, registering just one shutout.
The Brazilian – linked with a summer move to Liverpool – is unlikely to return given his contract dispute with the club, and his assuredness between the posts is undoubtedly missed.
At the other end, if their attacking players are contained then Fiorentina struggle, with the midfield contributing just seven goals this term. Meanwhile, they are no longer as deadly from set-pieces.
The game plan
Montella has shown that he is tactically flexible, often deploying a back three in domestic fixtures and using a variety of combinations up front depending on the opposition.
The coach has often utilised a 4-3-3 in Europe, with the likes of Salah, Khouma Babacar and veteran Spanish winger Joaquín offering plenty of attacking options.
Whatever their shape, the side’s biggest strength comes in midfield with Matías Fernández, Borja Valero and the seemingly ageless David Pizarro offering a superb blend of skill and steel. The constant probing of that trio seeks to release the pace ahead of them, while Gomez or Babacar lurk awaiting their moment to strike.
Borja Valero is the fulcrum of this side, maintaining a steady rhythm as the moving parts around him constantly change depending on Montella’s tactical choices.
Often overlooked by Spain due to their wealth of midfield options, the former West Brom and Villarreal star registered six goals and nine assists last term in a thoroughly impressive campaign.
Fiorentina’s struggles in the early part of the season have seen his statistical contribution drop somewhat, but his passing remains as crisp and incisive as ever.
No midfielder in Serie A has created as many goalscoring opportunities for his team-mates, and with the Viola running into form, Valero is once again at the heart of everything they do.
Outside of Serie A’s traditional giants, Fiorentina are perhaps the most well-known Italian team, their distinctive purple kits and rich history making them easily identifiable to even the most casual of fans.
They have won just two league titles, but have always been among the peninsula’s most prominent teams and were the first to contest a European final when losing to Real Madrid in 1957.
The Viola have a fine cup tradition, winning the Coppa Italia six times, while they also lifted the Cup Winners' Cup after beating Rangers back in 1961.
While those wins over Liverpool are fresh in the memory, older fans will remember Fiorentina’s Champions League run in 1999/00, when Argentine hero Batistuta was at his net-busting best.
His thumping strike from a tight angle handed them a famous victory over Arsenal at Wembley, before he also netted twice against the reigning champions Manchester United.
With 56 goals in just 78 appearances, the Argentine remains his country’s all-time leading scorer, and his 184 goals in 318 matches for La Viola ensured he is idolised in Italy too.
He stayed loyal to the club when they were relegated in 1993, prompting fans to erect a life-sized statue of the striker outside their stadium.