Parma entered the competition at the Round of 16 as the rules of the tournament dictated that, alongside those teams which qualified for Europe for the 2010–11 season, the highest finisher in Serie A who failed to qualify for European football would begin competing at that advanced stage. As the entirety of the tournament is pre-drawn, Parma knew the identity of the ten teams that would fight for the right to play away at the Ennio Tardini in the Round of 16 in the first four preliminary rounds. These were Santegidiese, Trapani, AlzanoCene, Reggiana, SPAL, Alessandria, all of whom competed from the First Round; Reggina, Frosinone, Empoli, all of whom competed from the Second Round; and Fiorentina, who competed from the Third Round. It transpired that Fiorentina – the only Serie A team in the section – emerged as Parma's opponents. The match remained goalless for 114 minutes until Fiorentina broke the deadlock through Mario Santana. Crespo equalised for Parma just a minute later and then scored another three minutes from time to take Parma through to the quarter-finals, where they faced Palermo away from home in the last week of January. The sides played out 120 minutes of goalless football before Palermo emerged victorious in a penalty shoot-out as Francesco Valiani missed the decisive penalty.