Pompey, who beat Championship side Cardiff in the Final last season, will be visited by Gary Johnson's men on the first weekend of the New Year.
City have been beaten by Premier League opposition in the last two seasons of the competition avoided Middlesbrough this year but a club spokesman said,
"It's obviously an interesting draw for us, but a tough one.
"To face the holders of the cup isn't the best draw we could have had but our supporters and team will make the journey full of hope, and I'm sure Gary will be playing up our chances."