Pompey have been drawn at home to fellow League Two side Accrington in the second round of the Emirates FA Cup.
The tie will be played at Fratton Park on the weekend of December 4-7.
The sides have already met on the south coast in the league this season, playing out a goalless draw back in September.
But they have not clashed in the FA Cup since being drawn together in the fourth round in January 1959.
Ron Saunders’ brace and strikes from Derek Weddle and Ron Newman helped secure a 4-1 victory in a Fratton replay following a goalless draw at Accrington.
The Blues also triumphed 5-2 when the sides met in a third round encounter in 1925.
Emirates FA Cup second round draw
Aldershot Town or Bradford City v Chesham United
Barnet v Brackley Town or Newport County
Peterborough United v Luton Town
POMPEY v Accrington Stanley
Stourbridge v Eastleigh
Northampton Town v Northwich Victoria or Boreham Wood
Exeter City v Port Vale or Maidenhead United
Cambridge United v Doncaster Rovers
Grimsby Town v Shrewsbury Town
Yeovil Town v Stevenage
Rochdale v Bury
Welling United v Carlisle United
Leyton Orient v Scunthorpe United
Millwall v Wycombe Wanderers
Colchester United v Altrincham
Chesterfield v Walsall
Sheffield United v Mansfield Town or Oldham Athletic
Salford City v Hartlepool United
Dagenham & Redbridge or Morecambe v Whitehawk
Braintree Town or Oxford United v Forest Green Rovers