Pompey have been drawn away to Chelsea U21s in the third round of the Checkatrade Trophy.
The tie is scheduled to be played at Stamford Bridge in the week commencing January 8.
As an invited club, at least six of the hosts' team must be aged 21 or under.
Chelsea reached this stage of the competition by finishing second in Southern Group D and then winning 4-0 at MK Dons in the last 32.
| Round 3 South |
| Yeovil Town v Forest Green Rovers |
| Chelsea U21 v Pompey |
| Charlton Athletic v Oxford United |
| Luton Town v Peterborough United |
| Round 3 North |
| Oldham Athletic v Leicester City U21 |
| Rochdale v Lincoln City |
| Bury v Fleetwood Town |
| Shrewsbury Town v Blackpool |