Pompey have been drawn away to Chesterfield in the first round of the Emirates FA Cup.
The tie wll be played at the SMH Group Stadium on the weekend of November 3-6.
It will see the Blues come up against their League Two title-winning manager Paul Cook, who is in charge of the Spireites.
They currently sit top of the National League standings after dropping just seven points from the opening 15 games.
Chesterfield eased into the first round proper after thrashing Kettering 5-0 on home soil at the weekend.
Former Pompey skipper Tom Naylor was among the scorers in that game, while Michael Jacobs also plays for the Derbyshire outfit, who have Gary Roberts on their coaching staff.
The only previous FA Cup meeting between the sides was a third round contest in January 1969.
It was the Blues who emerged 3-0 winners in that Fratton Park clash, courtesy of a Nick Jennings brace and Albert McCann strike.
It finished goalless when Pompey – then managed by Richie Barker – last visited Chesterfield's patch for a League Two fixture in March 2014.
A confirmed date for the game and ticket information will be announced in due course.
| Emirates FA Cup first round draw |
| Curzon Ashton v Aveley or Barnet |
| Alfreton Town v Worthing |
| Chesterfield v POMPEY |
| Bolton Wanderers v Solihull Moors |
| Exeter City v Wigan Athletic |
| Leyton Orient v Carlisle United |
| Kidderminster Harriers v Fleetwood Town |
| Hereford v Gillingham |
| Ebbsfleet United or Slough Town v Grimsby Town |
| Charlton Athletic v Cray Valley (PM) |
| Oxford United v Maidenhead United |
| Newport County v Oldham Athletic |
| Swindon Town v Aldershot Towb |
| Crewe Alexandra v Derby County |
| Mansfield Town v Wrexham |
| Marine v Harrogate Town |
| Barnsley v Horsham |
| Port Vale v Burton Albion |
| Peterborough United v Salford |
| Eastleigh v Boreham Wood |
| Bradford City v Wycombe Wanderers |
| Billericay Town or Sheppey United v Walsall |
| Shrewsbury Town v Colchester United |
| Bristol Rovers v Chelmsford City or Whitby Town |
| Lincoln City v Morecambe |
| Sutton United v AFC Fylde |
| Reading v Milton Keynes Dons |
| Doncaster Rovers v Accrington Stanley |
| Chester v York City or Needham Market |
| Scarborough Athletic or Oxford City v Forest Green Rovers |
| Notts County v Crawley Town |
| Stockport County v Worksop Town |
| Yeovil Town v Gateshead |
| Stevenage v Tranmere Rovers |
| Braintree Town or Chesham United v Maidstone United |
| Bromley v Blackpool |
| AFC Wimbledon v Cheltenham Town |
| Cambridge United v Bracknell Town |
| Northampton Town v Barrow |
| Ramsgate v Hemel Hempstead Town or Woking |