Pompey have been drawn at home to League Two side Northampton in the second round of the Leasing.com Trophy.
The tie is scheduled to take place at Fratton Park in the week commencing December 2.
The only previous meeting between the sides in this competition came back in 2014, with the Cobblers winning 2-1 on the south coast.
Keith Curle's outfit currently sit ninth in the fourth tier and finished runners-up behind Peterborough in Southern Group H.
Pompey – who beat Sunderland in last season's Wembley final – had guaranteed a home tie by topping Southern Group B.
| Leasing.com Trophy R2 (Southern Section) |
| Colchester United v Stevenage |
| Walsall v Chelsea U21 |
| Brighton & Hove Albion U21 v Newport County |
| POMPEY v Northampton Town |
| Milton Keynes Dons v Coventry City |
| Exeter City v Oxford United |
| Peterborough United v Ipswich Town |
| Bristol Rovers v Leyton Orient |
| Leasing.com Trophy R2 (Northern Section) |
| Port Vale v Mansfield Town |
| Accrington Stanley v Bolton Wanderers |
| Leicester City U21 v Doncaster Rovers |
| Salford City v Wolverhampton Wanderers U21 |
| Everton U21 v Fleetwood Town |
| Manchester City U21* v Shrewsbury Town |
| Blackpool v Scunthorpe United |
| Manchester United U21* v Tranmere Rovers |
*Manchester City U21 and Manchester United U21 have been granted dispensation to play knockout games away from home, so these ties will be reversed.