Pompey have been drawn at home to non-league Macclesfield Town in the first round of the FA Cup.
Paul Cook’s side were drawn out of the hat late in the draw to host the Vanarama National League outfit, who are currently in mid-table.
Pompey crashed out to non-league opposition last season when they were knocked out by Aldershot Town in a replay and will be keen to avoid a repeat.
The Hawks, meanwhile, face a replay with Cheltenham after their battling draw at the weekend.
But if they do come through that clash, a lengthy trip to Hartlepool United awaits the winners.
The ties will be played over the weekend of November 7/8.