The Spaniard has won a trophy with each of his last four clubs and could continue that run with victory this weekend
He has enjoyed relative success in his maiden season at the club, all but securing a return to the Champions League for next season, a competition from which they suffered a narrow exit in the group stages this term.
Benitez has won a trophy with each of the last four clubs he has managed and is on the brink of continuing that streak with Napoli at the Stadio Olimpico.
But the 2012 winners face a stern test if they are to regain the trophy against a Fiorentina team who represent their only competition for Serie A's final Champions League spot, and who will be desperate to end a 13-year wait for silverware.
Fiorentina's hopes of bridging the eight-point gap to Napoli in the race for a spot in Europe's premier club competition are slim, but Vincenzo Montella's men should approach the final with confidence having won in Naples in March.
The Florence club's last piece of silverware came in the Coppa Italia when they beat Parma over two legs back in 2001, and Montella will be able to welcome back captain Manuel Pasqual and striker Alessandro Matri from suspension as they look to win the trophy for a seventh time.
However, Juan Cuadrado misses out with a ban following a booking in the second leg of the semi-final with Udinese.
It is not known whether long-term absentee Giuseppe Rossi (knee) will deliver on his promise to return in time for the final, while Mario Gomez (knee), Gonzalo Rodriguez (illness) and goalkeeper Neto (hand) are all doubts.
Matias Fernandez and Ante Rebic have returned to training but are questionable to feature in the Italian capital.
Meanwhile, Napoli could head into the game without star striker Gonzalo Higuain, who suffered a bruised shin in last week's 0-0 draw at Inter, although Christian Maggio is fit to return following nearly two months on the sidelines.