Bari 2 – Bassano Virtus 0 (Coppa Italia, August 16, 2008) Bari secured the win in the final 20 minutes of the match, Barreto put the hosts ahead from the spot before Barreto bagged his second three minutes later with a tidy finish in the box.
Parma 3 – Portogruaro 2 (Coppa Italia, August 16, 2008) Parma almost got a shock when the Serie C outfit took a commanding 2-0 lead through Cunico on 35 minutes and substitute Maniero on the hour mark. Massimo Paci got Parma back into the game, but it took a last-gasp equaliser from Stefano Morrone to force extra time, where Daniele Paponi popped up with the winner.
Albinoleffe* 2 – Pescara 2 (Pens. 6-5) (Coppa Italia, August 16, 2008) Albinoleffe struggled to get past third division Pescara, needing penalties to get into the third round.