Pompey have been drawn away to Southend in the third round of the Checkatrade Trophy.
The tie will be played at Roots Hall in the week beginning January 7.
Pompey are looking to make it through to the quarter-finals, having fallen to Chelsea U21s at this stage last season.
| Checkatrade Trophy Round Three (South) |
| Southend v POMPEY |
| Chelsea U21 v Peterborough |
| Cheltenham v Oxford or Tottenham U21 |
| Northampton v Bristol Rovers |
| Checkatrade Trophy Round Three (North) |
| Rochdale or Oldham v Man City U21 |
| Sunderland v Newcastle U21 |
| Accrington v Bury |
| Port Vale v Shrewsbury |