Blues paired with Gulls in first round draw
Pompey have been drawn away to Torquay United in the first round of the Johnstone’s Paint Trophy.
The match will be played at Plainmoor in the week commencing September 2.
Pompey have not faced the Gulls since a two-legged League Cup first round tie in August 1999.
Following a goalless draw at Plainmoor, the Blues won 3-0 at Fratton Park – with goals from Luke Nightingale (2) and Steve Lovell – to progress.
The sides have met nine times in total, with Pompey winning six, Torquay triumphing twice and one draw.
They will also play twice in League Two this term, with matches at Plainmoor in October and Fratton Park in February.
The Blues reached the second round of the Johnstone’s Paint Trophy last season, defeating Bournemouth on penalties before going out to Wycombe.
Torquay crashed out at the first hurdle, losing at home to Yeovil on penalties.
Johnstone's Paint Trophy first round draw
Shrewsbury Town v Oldham Athletic
Crewe Alexandra v Accrington Stanley
Tranmere Rovers v Fleetwood Town
Port Vale v Bury
Notts County v Burton Albion
Scunthorpe United v Sheffield United
Hartlepool United v Bradford City
Wolverhampton Wanderers v Walsall
Torquay United v POMPEY
Bristol City v Bristol Rovers
Exeter City v Wycombe Wanderers
Cheltenham Town v Plymouth Argyle
Milton Keynes Dons v Northampton Town
Dagenham & Redbridge v Colchester United
Gillingham v Leyton Orient
Brentford v AFC Wimbledon
Northern Section byes
Preston North End
Southern Section byes