The Azzurri and Cristiano Ronaldo’s Portugal both finished second in their qualifying groups, behind Switzerland and Serbia respectively.
Italy will host North Macedonia in the play-off first round in March, with Turkey visiting Portugal, before the winners face off for a spot at next year’s finals in Qatar.
The draw means that one of the last two European Championship winners will not be at the next World Cup. Portugal won the Euro 2016 title.
The winners of Portugal’s match with Turkey will host the final-round game in Path C.