The victory -- after a completely bizarre match -- sets up a meeting with Inter Milan in the next round.
The strangeness begun with the earth-shattering news that AS Roma coach Zdenek Zeman had deviated from his beloved 4-3-3 for the first time since his tenure in charge of Lecce in 2004-05, matching Fiorentina’s 3-5-2 in an interesting 3-4-3 formation.
In terms of team selection, Fiorentina went full strength while Roma took the opportunity to engage in some squad rotation. The injury-forced absence of Osvaldo combined with Zeman taking the opportunity to rest the giallorossi's star and starlet Francesco Totti and Erik Lamela respectively, making Mattia Destro the central striker alongside Alessandro Florenzi and Miralem Pjanic.
It was the visitors who had the first real chance, with Daniele De Rossi glancing a Pjanic header just wide of the far post. Stevan Jovetic blazed the ball over the bar moments later in Fiorentina’s first snapshot in a lively start to the match.
The scores somehow stayed level after the best of the early chances a couple of minutes later, when Florenzi was slipped through by Michael Bradley, forcing a diving save from Fiorentina keeper Neto. The rebound fell sweetly for Pjanic, though his well-struck volley was blocked by Gonzalo Rodríguez.
Despite the viola enjoying more possession and featuring enough playmakers in their starting eleven to give Max Allegri nightmares, they struggled for the final cutting pass -- partly down to the uncharacteristically solid Roma defence.
Just short of the half hour Destro had Roma’s third good chance of the match when he connected with a Bradley tackle in the Fiorentina third. The young striker dribbled the ball around Rodríguez well, though dragged his shot just wide of the far post.
It was telling of Fiorentina’s lack of penetration that they went closest with a free-kick in the first half, with ex-Roma midfielder -- and boyhood giallorossi fan -- Alberto Aquilani rattling the bar from an excellent set piece five minutes before the break.
After the restart Roma had another outstanding opportunity, though once again down to their own profligacy they couldn’t break the deadlock. Mattia Destro squared across the box for Florenzi, whose effort allowed the Brazilian goalkeeper to save when he really shouldn’t have been given the chance.
As the game drew ever closer to extra time, Fiorentina looked increasingly dangerous with the game opening out. But despite their frequent crosses into the area they just couldn’t score, and when De Rossi headed in from a free-kick with just over ten minutes remaining, it seemed it was curtains. However, the Roma captain was adjudged to have been offside, and parity was restored.
Destro’s finishing was less clinical than a farmyard, and he failed to make the viola pay for another defensive mistake inside the final ten minutes. That chance, though, had nothing on those created in a crazy final minute of stoppage time.
Just as the clock hit 92, the ball fell perfectly for Borja Valero, who crashed the ball on the volley against the corner of bar and post, before Roma went up the other end and found Destro. The ex-Siena striker lofted the ball over Neto, though a goal-line intervention from Stefan Savic meant the scores stayed level and the game was going to extra time.
Fiorentina continued the first period where they left off, though when a goal was finally scored, it wasn’t the hosts who netted it. Roma decided the best policy was to give Destro a chance that he couldn’t miss, so when Pjanic squared from the right after a quick counter-attack, the forward just had to tap the ball over the line for 1-0, getting one over on his former club's fiercest rivals.
But, true to form, that wasn’t the final chance of the match. In quick succession Aquilani forced a great save from Mauro Goicoechea via a free kick and Juan Cuadrado struck a volley against the post from point-blank range in Fiorentina’s third rendezvous with the woodwork. Coach Vincenzo Montella did, however, resist the urge to strap his own boots to boost his side's chances of finding the net.
Roma continued to withstand the purple haze attacking them from all angles, and not even the sending off of substitute Rodrigo Taddei for a very slight touch in the dying moments was enough for Fiorentina to finally find the net, as the game completely descended into chaos in scenes only Italy could produce.
Juan Cuadrado and Dodo were sent off for being the instigators of an amusing brawl, before the referee finally blew the final whistle.
Fiorentina (3-5-2): Neto; Nenad Tomovic, Gonzalo Rodríguez, Stefan Savic; Manuel Pasqual (Cristian Llama 106), Borja Valero, Giulio Migliaccio (Romulo 65), Alberto Aquilani, Juan Cuadrado; Luca Toni (Adem Ljajic 78), Stevan Jovetic
Roma (3-4-3): Mauro Goicoechea; Marquinhos, Leandro Castan, Nicolas Burdisso; Federico Balzaretti (Dodo 59), Michael Bradley, Daniele De Rossi, Ivan Piris (Rodrigo Taddei 81); Alessandro Florenzi, Mattia Destro, Miralem Pjanic (Panagiotis Tachtsidis 101)
Goals: Destro 97 (R)
Red cards: Taddei 117 (R) Cuadrado 122 (F) Dodo 122 (R)