Pompey have been drawn away to non-league Harrogate Town in the first round of the FA Cup.
The Blues will make the trip to the National League outfit over the weekend of November 8-11.
Kenny Jackett’s troops were 4-0 winners at another National League side, Maidenhead United, at the same stage last term.
Simon Weaver’s Harrogate team booked their spot in the first round after winning 2-1 at league rivals Halifax Town on Saturday.
Town sit eighth in the National League, just a point off the play-off places.
Pompey, who enter the competition at this stage, reached round four last season before they were knocked out in a replay at Championship outfit QPR.
Meanwhile, Isthmian League South East side Chichester City – the lowest ranked team left in the competition – received a bye to the second round due to Bury’s expulsion from the EFL.