Despite playing some of the best football in Italy last season at the Stadio Artemio Franchi, Fiorentina's campaign was defined by that heartbreak in Siena.
The Viola claimed that they were never striving for a Champions League place and that, by finishing fourth—obtaining a Europa League place in the process—Vincenzo Montella had overachieved with a side that had only narrowly beat off relegation a year earlier.
Having come minutes away from beating Milan to that much-coveted third place, the Viola had to watch on, helpless, as the Rossoneri came from behind to snatch that much-coveted third spot.
The implications were massive, but Fiorentina have managed to embrace the inevitable departure of their best player, Stevan Jovetic.
The Montenegrin departed for Manchester City in a deal that could eventually be worth as much as £28 million according to the Daily Mail, which seems small change when you consider the money that Napoli managed to squeeze out of Paris Saint-German for their star striker Edinson Cavani.
Jojo might not be in El Matador's class just yet, but he is pretty close and certainly better than the disparity in the two transfer fees might suggest, but the Viola arguably made better use of their cash in the mercato than the Partenopei—even if Rafael Benitez will be pleased with the Partenopei's business too.
One positive that has been understated this summer is maintaining L'Aeroplanino as their manager. After three clubs in as many seasons, Montella remained loyal to the cause and has set the ambitious target of reaching the Champions League.
The Viola made a profit this summer, bringing in revenue from the sales of Adem Ljajic and Haris Seferovic on top of that of Jovetic.
Purchases included Mario Gomez, Josip Ilicic, Joaquin, Massimo Ambrosini, Juan Cuadrado on a permanent basis and young starlets Ante Rebic and Marko Bakic.
While Milan might have made a last ditch swoop for Kaka, Fiorentina remain a more rounded squad who should feel comfortable enough in their initial target of usurping the Rossoneri into third place.
Now the question is whether Montella can exceed all expectations and challenge Napoli and even Juventus, who will both have Champions League matches to juggle with their domestic schedule.
While Montella's men have the Europa League, unquestionably that competition will be used as merely a way of providing fringe players with extra minutes on the field, so it should not hurt their charge in the league.
It remains a push to expect Montella to sustain a title challenge, but do not bet against Fiorentina being a factor, especially given the tumultuous changes in Naples, which could see some teething problems, especially once European football kicks into play.
Outside of the Old Lady, Fiorentina are the most settled group, with a positive footballing philosophy that will not leave them wondering as to whether they might have been able to make a title tilt.
With tactical versatility to be able to switch between systems with a back three and a back four, we can expect Fiorentina to be able to handle all opponents this season.
The purchases of Joaquin and the renaissance of Giuseppe Rossi ought to be able to maintain a wide threat when Montella opts to use Cuadrado and Manuel Pasqual as full-backs.
With such a vast number of tactical options on display in Italian football, Montella has even experimented with a diamond formation in order to maintain last season's magical trio of centre-midfielders—Borja Valero, David Pizarro and Alberto Aquilani—as well as accommodating the experienced war horse Ambrosini.
The heart of the defence and the ongoing goalkeeping dilemma remain issues that will concern Montella though.
But Gonzalo Rodriguez remains one of Serie A's top defenders, and there is the possibility that an ever-improving Stefan Savic, at 22 years old, brings his game to a new level this season with more regular minutes on the pitch.
Facundo Roncaglia started his career in Italian football magnificently, but his form tailed off towards the end of the season. If the Argentine can rediscover that form then Fiorentina should be well set, but if the former Boca star continues to struggle, it may be the side's downfall, as neither Nenad Tomovic or Marvin Compper appear good enough to seize that third place in the back three on a regular basis.
The young Brazilian goalkeeper Neto has confidence issues, but like Arsenal's Wojciech Szczesny, the raw tools are there to blossom into a fine stopper if the club show him enough faith, which appears to be the case.
Despite these deficiencies at the back, I hold out hope that Fiorentina can indeed hold onto the tails of Juve, at least until the Christmas break. With firepower like Rossi and Gomez, who have already scored five times between them, the Viola will be able to win an awful lot of games.
Their pass-and-move style of football will fashion an abundance of opportunities in front of goal, and that pairing will put them away on a far more regular basis that Jovetic or Ljajic would have done.
Juve are clearly the team to beat, but Fiorentina have quietly assembled a side with enough quality to potentially be their closest rival, which makes Florence one of European football's must-see destinations this season.