Empoli progressed to the Coppa Italia quarter-finals at the expense of Fiorentina after a 2-2 game across the 90 minutes and a 4-3 penalty shootout victory for the visitors in testing circumstances at the Stadio Franchi.
Emmanuel Ekong opened the scoring after four minutes, which Moise Kean and Riccardo Sottil responded to in the second half, only for Sebastiano Esposito to draw Empoli level again 15 minutes before full-time.
Kean and Luca Ranieri missed the crucial spot kicks for Fiorentina, while Esposito converted the winning spot kick to send his side through to the last eight.
See how it all unfolded on the Football Italia LIVEBLOG.
Raffaele Palladino made minimal changes to his team that played for 17 minutes against Inter in Serie A on Sunday, while Roberto D’Aversa went with a youthful Empoli side that included 18-year-old Lorenzo Tosto and 20-year-old Luca Marianucci in the back three.
There were plenty of tributes for Edoardo Bove ahead of kick-off. The 22-year-old collapsed in the 17th minute of Fiorentina’s Serie A match against Inter on Sunday and remains in intensive care, although he has been awake and alert since Monday.
There was a tifo from the Curva Nord, who held his shirt number aloft from the stands, while the Fiorentina players and staff held up banners before kick-off, one of which read: ‘We’ll wait for you, Edo’
It took just four minutes of action for the deadlock to be broken. Lucas Martinez Quarta gave the ball away in a central area, 40 yards out from his own goal, which allowed Ekong to pounce and dispatch a routine finish past Pietro Terracciano when one-on-one.
It took a little while for Fiorentina to recover from their early slip. Dodo tried to get his team going with an incredible run after 17 minutes, starting in his own half and ending up on the left byline. His cross was steered onto the crossbar by Kean.
It would be Kean, again, to put Fiorentina back on level terms. A neat exchange between Riccardo Sottil and Amir Richardson in the area forced a save from Jacopo Seghetti in the Empoli net, and the Italy international was on hand to stab home the rebound from two yards out.
Sottil thought he had handed Fiorentina the victory with just under 20 minutes to go. He collected the ball on the left flank before cutting in and dispatching an effort into the far corner, although it did take a nick off Robin Gosens on the way in.
Empoli were level again just a few minutes later, though. Liam Henderson’s ball fed Esposito one-on-one. The Italian made no mistake in delicately lifting it over Pietro Terracciano to level the scores again. Kean came within millimetres of putting Fiorentina ahead just before the 90th minute, but goal line technology deemed that he had not scored, nor had Ardian Ismajli, who almost put one in for an own goal in the follow-up.
With the scores level at full-time, the game went straight to penalties, rather than extra time.
The first three penalties were successfully converted. Albert Gudmundsson, Lorenzo Colombo and Christian Kouame all converted, before Ekong made the first error.
Luca Ranieri then missed his penalty and Liam Henderson squeezed his in to draw the shootout level after three kicks each.
Kean missed in spectacular fashion, blazing his effort up and over and way into the stands. Luca Marianucci then scored his to put Empoli 3-2 up in the shootout.
Cataldi scored Fiorentina’s next one, but it was already out of La Viola’s hands by that point. Esposito was up next and blasted one straight fown the middle to send his side through as 4-3 winners in the shootout.
Empoli will face the winner of Juventus-Cagliari in the quarter-final.
Full-time: Fiorentina 2-2 Empoli (3-4 on penalties)
Ekong (E) 4′, Kean (F) 59′, Sottil (F) 70′, Esposito (E) 75′.
Penalties scored
Fiorentina: Gudmundsson, Kouame, Cataldi.
Empoli: Colombo, Henderson, Marianucci, Esposito.
Penalties missed
Fiorentina: Ranieri, Kean.
Empoli: Ekong.