Pompey have been drawn to face League Two side Luton away in the first round of the Emirates FA Cup.
The tie will be played at Kenilworth Road on the weekend of November 3-6.
It is the first meeting between the sides in this competition since the Blues were beaten 3-1 in a quarter-final clash in 1988.
In fact, the Hatters have a perfect FA Cup record against Pompey, also triumphing in 1922 – following a replay – and 1951.
But the Blues came out on top in both League Two contests last term – including an impressive 3-1 victory at Kenilworth Road – on their way to the title.
Luton are aiming to follow in their footsteps and currently sit third in the table following a 7-1 rout of Stevenage at the weekend.
"It's a tie between two really big clubs and it's one that I'm quite excited about."
Both sides fell at the first hurdle in last season's FA Cup, with the Hatters losing at Exeter, while Pompey were beaten at home by Wycombe.
Assistant manager Joe Gallen said: "It's a tie between two really big clubs and it's one that I'm quite excited about actually.
"We won there with Millwall on our way to the semi-finals in 2013, but I know that it's always a difficult place to visit because it's a tight ground.
"But with the way we're playing at the moment, we're confident of going anywhere and getting a positive result, so hopefully we can progress to the second round."
|Emirates FA Cup first round draw|
|Stevenage v Nantwich Town or Kettering Town|
|Bradford City v Chesterfield|
|Port Vale v Oxford United|
|Newport County v Walsall|
|Morecambe v Hartlepool United|
|Yeovil Town v Southend United|
|Peterborough United v Tranmere Rovers|
|Cambridge United v Sutton United|
|Forest Green Rovers v Macclesfield Town|
|AFC Fylde v Kidderminster Harriers|
|Luton Town v POMPEY|
|Shrewsbury Town v Aldershot Town|
|Hereford v AFC Telford United|
|Guiseley v Accrington Stanley|
|Blackburn Rovers v Barnet|
|East Thurrock United or Ebbsfleet United v Doncaster Rovers|
|Leatherhead v Brackley Town or Billericay Town|
|Boreham Wood v Blackpool|
|Shaw Lane Association v Mansfield Town|
|Colchester United v Oxford City|
|Plymouth Argyle v Grimsby Town|
|AFC Wimbledon v Lincoln City|
|Rochdale v Dover Athletic or Bromley|
|Coventry City v Maidenhead United|
|Chorley or Boston United v Fleetwood Town|
|Carlisle United v Oldham Athletic|
|Notts County v Bristol Rovers|
|Dartford v Swindon Town|
|Cheltenham Town v Maidstone United or Enfield Town|
|Woking or Concord Rangers v Bury|
|Crewe Alexandra v Rotherham United|
|Gillingham v Dagenham & Redbridge or Leyton Orient|
|Hyde United v Milton Keynes Dons|
|Gainsborough Trinity v Slough Town|
|Solihull Moors or Ossett Town v Wycombe Wanderers|
|Northampton Town v Scunthorpe United|
|Charlton Athletic v Truro City|
|Wigan Athletic v Crawley Town|
|Gateshead v Bath City or Chelmsford City|
|Exeter City v Heybridge Swifts|