The European debut for Milano will be remembered by a defeat. On their away match against Omonia Nicosia, Milano have been defeated 2-0, with goal coming in each half. The return leg is scheduled for 31.07.2008 Unsuccesful debut for the vice-champions in UEFA cup. Milano lost 2-0 against Omonia in the first qualifying round of the UEFA cup. The match started with a chance for the visitors, but soon after Omonia took the control of the match and were dominating. In the 20th minute, Kukaj headed the ball into his own net and that meant 1-0 lead for the hosts. Until the end of the first half both teamc created several smaller chances, but the result remained unchanged. Right at the beginning of the second half, Omonia had another good chance, but the ball sailed past the goal. 20 minutes into the second half and the final score had been set. Zlogar headed one ball home and that had already been a solid lead for the hosts. Later, Manevski had one good chance for Milano, but the result remained the same. Omonia have brought the match to end with routine and were denying Milano's attempts for attack.

Omonia: Georgallides, Wenzel, Maris, Pletsch, Zlogar, Kaseke, Duro, Clayton* (Pavlou 85'), Charalambous, Christofi* (Bangura 72'), Cafu* (Vasconcelos 80').
Milano: Nuredinoski, Ristov, Kukaj, Lazarevski, Alimi* (Limani 78') , Gasi, Manevski, Gligorovski* (Sali 59'), Isufi, Gligorovski, Trajcev.