Udinese, Sampdoria and Napoli booked their places in the quarter-finals of the Coppa Italia.
Udinese squeezed through after a dramatic penalty shoot-out win over Serie A rivals Reggina. In a hard-fought encounter Udinese had two men sent off before prevailing 8-7 on penalties after sudden death.
Reggina missed a great chance to win the game in the 90 minutes when they won a penalty after Emanuele Belardi was sent off for bringing down Dorde Rakic.
Emil Halfredsson failed from the penalty spot two minutes from time by blazing his attempt over the crossbar.
Udinese were reduced to nine men two minutes before the end of extra-time when substitute Fabio Quagliarella was dismissed for a dangerous tackle from behind.
Neither side could find a winner meaning the game went into a dreaded penalty shoot-out.
With the shoot-out tied at 7-7 and in sudden death Aleksandar Lukovic scored to put Udinese ahead putting all the pressure on Luca Tognozzi who missed his spot-kick to send Udinese through.
Sampdoria progressed into the last eight with a 2-1 victory over Serie B promotion-chasing Empoli.
Emiliano Bonazzoli gave Sampdoria the lead just past the half-hour mark, but they were reduced to ten men when Daniele Dessena was sent off for a second bookable offence after 36 minutes.
Despite their numerical disadvanatage Bruno Fornaroli doubled Samp's lead from the penalty spot right on the stroke of half-time.
Francesco Lodi pulled a goal back for Empoli just past the hour mark before Reto Ziegler missed from the penalty spot 14 minutes from time for the hosts to extend their lead.
Napoli eased into the quarter-finals with a 3-1 victory over local rivals Salernitana.
The Azzurri were gifted the lead on 16 minutes when Maurizio Peccarisi put through his own net and Inacio Pia added a second nine minutes later.
Arturo Di Napoli gave Salernitana hope with a goal five minutes after the break, but Marek Hamsik's penalty three minutes later ended any chances of a comeback from the visitors.
The remaining Last 16 ties are scheduled for December and January.
Round 5 Results
Wednesday 12 November
Udinese 0-0 Reggina AET (Pens: 8-7)
Sampdoria 2-1 Empoli
Napoli 3-1 Salernitana
Round 5 Fixtures
Wednesday 3 December
Milan v Lazio (1945)
Wednesday 17 December
Fiorentina v Torino (1600)
Roma v Bologna (2000)
Tuesday 13 January
Inter v Genoa (2000)
Wednesday 14 January
Juventus v Catania (1945)
Wednesday 21 January, 4 February
Inter/Genoa v Roma/Bologna
Milan/Lazio v Fiorentina/Torino
Napoli v Juventus/Catania
Sampdoria v Udinese
[Coppa Italia 2008-09 Draw]
Coppa Italia Fifth Round Review:
[Wednesday 12 November] – [Wednesday 3 December] – [Wednesday 17 December] - [Tuesday 13 January] - [Wednesday 14 January]
Source: Sky Sports / Lega Calcio