Roberto Mancini admitted Italy would rather not have to do battle with Portugal for a place in the 2022 World Cup if they get past North Macedonia.
The European champions were on Friday drawn to face North Macedonia in a semi-final next March after missing out on automatic qualification for the tournament in Qatar.
Italy will come up against either Portugal or Turkey in a decisive showdown if they avoid a semi-final upset.
Euro 2016 champions Portugal were consigned to a play-off spot in dramatic fashion as Aleksandar Mitrovic's last-gasp strike saw Serbia through as Group A winners.
Italy boss Mancini is confident his side will qualify, but gave an honest reaction to the prospect of trying to deny Cristiano Ronaldo what could be his last trip to a World Cup.
He said: "We are always confident and positive. Macedonia had a good qualifying group, we will have to play a great match. Then we will see what happens in the final.
Asked about the prospect of coming up against Portugal, he said: "We would have liked to avoid them, in the same way Portugal would have gladly avoided Italy."
The draw also threw up the possibility of Wales going up against Scotland for a place in the finals, should they overcome Austria and Ukraine.
Russia will host Poland, with the winners playing either Sweden or the Czech Republic.