Husih Park trip for Pompey in first roundPompey have been drawn away to League One outfit Yeovil Town in the first round of the Johnstone's Paint Trophy.
The tie will be played at Huish Park in the week beginning Monday, September 1.
Pompey have only played the Glovers competitively on two previous occasions.
The Blues won 2-1 away in a League One clash in October 2012, but lost the return fixture two months later.
This is Pompey's third season competing in the Johnstone's Paint Trophy and they reached the area quarter-finals last term, beating Torquay and Oxford before losing at Newport.
Johnstone's Paint Trophy first round draw
Preston North End v Shrewsbury Town
Accrington Stanley v Carlisle United
Crewe Alexandra v Rochdale
Fleetwood Town v Morecambe
Oldham Athletic v Bradford City
Barnsley v York City
Scunthorpe United v Chesterfield
Notts County v Mansfield Town
Wycombe Wanderers v Coventry City
Newport County v Swindon Town
Yeovil Town v POMPEY
Cheltenham Town v Oxford United
Crawley Town v Cambridge United
Peterborough United v Leyton Orient
AFC Wimbledon v Southend United
Stevenage v Gillingham