Blues draw Championship side
Pompey have been drawn away to Championship side Cardiff in the first round of the Carabao Cup (EFL Cup).
The tie will be played at Cardiff City Stadium in the week beginning August 7.
The sides last met in this competition in November 2004, when Yakubu's brace at Ninian Park sent the Blues into the quarter-finals.
Pompey also triumphed in 1990, while the Bluebirds were victorious in both 1965 and 1995.
The most recent trip to Cardiff City Stadium was for a Championship clash in January 2012.
It was an eventful affair, with the Welsh side scoring a last-gasp winner, despite Marko Futacs and Greg Halford both finding the target for the visitors.
Pompey were also away at this stage of last season's competition. Goals from Curtis Main and Kal Naismith took Coventry to extra-time, but it was the hosts who ultimately triumphed.
Cardiff similarly exited at the first hurdle, suffering a 1-0 defeat at Bristol Rovers.
Manchester United are the current holders of the EFL Cup, following their 3-2 victory over Southampton at Wembley back in February.
Carabao Cup first round draw
|Birmingham City v Crawley Town|
|Exeter City v Charlton Athletic|
|Queens Park Rangers v Northampton Town|
|Newport County v Southend United|
|Bristol City v Plymouth Argyle|
|Cardiff City v POMPEY|
|Millwall v Stevenage|
|Oxford United v Cheltenham Town|
|AFC Wimbledon v Brentford|
|Norwich City v Swindon|
|Bristol Rovers v Cambridge United|
|Peterborough United v Barnet|
|Wycombe Wanderers v Fulham|
|Colchester United v Aston Villa|
|Wolverhampton Wanderers v Yeovil Town|
|Reading v Gillingham|
|Forest Green Rovers v Milton Keynes Dons|
|Luton Town v Ipswich Town|
|Coventry City v Blackburn Rovers|
|Nottingham Forest v Shrewsbury Town|
|Bradford City v Doncaster Rovers|
|Mansfield Town v Rochdale|
|Grimsby Town v Derby County|
|Barnsley v Morecambe|
|Crewe Alexandra v Bolton Wanderers|
|Oldham Athletic v Burton Albion|
|Wigan Athletic v Blackpool|
|Bury v Sunderland|
|Sheffield Wednesday v Chesterfield|
|Accrington Stanley v Preston North End|
|Fleetwood Town v Carlisle United|
|Sheffield United v Walsall|
|Scunthorpe United v Notts County|
|Rotherham United v Lincoln City|
|Leeds United v Port Vale|