Lazio booked a spot in the quarter-finals of the Coppa Italia after a 2-1 win at AC Milan after extra-time.
Milan overcame Emerson's red card to take the lead at the San Siro, only for Mauro Zarate to hit a late equaliser before Goran Pandev netted early in the first extra period.
With four more ties yet to be played, Lazio join Napoli, Sampdoria and Udinese in the last eight.
After a tight first half, Milan were reduced to 10 men midway through the second period when Emerson was sent off for picking up two bookings in the space of six minutes.
Yet within four minutes of the Brazilian midfielder's dismissal, the Rossoneri were in front as Andriy Shevchenko fired home a cracking shot.
The lead lasted until three minutes from the end when Zarate converted from the penalty spot after Pandev was brought down by Giuseppe Favalli.
And, just two minutes into extra-time, Lazio sealed a quarter final spot after Macedonian striker Pandev pounced on the rebound after Nelson Dida had parried Zarate's shot.
Lazio will now play the winners of Fiorentina and Torino, that is played next week.
Round 5 Results
Wednesday 12 November
Udinese 0-0 Reggina AET (Pens: 8-7)
Sampdoria 2-1 Empoli
Napoli 3-1 Salernitana
Wednesday 3 December
Milan 1-2 Lazio AET
Round 5 Fixtures
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
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