Pompey will host Arsenal U21s in the second round of the Checkatrade Trophy.
The tie is scheduled to take place at Fratton Park in the week beginning December 3.
Kenny Jackett's side were guaranteed a home fixture after winning all three games to take top spot in Southern Group A.
Pompey have not faced a Gunners side since losing 4-1 in a Premier League clash at Fratton Park in December 2009.
An exact date for the tie and ticket information will be announced in due course.
| Checkatrade Trophy Second Round – South |
| Chelsea U21 v AFC Wimbledon |
| POMPEY v Arsenal U21 |
| Cambridge United v Northampton Town |
| Exeter City v Peterborough United |
| Cheltenham Town v Newport County |
| Luton Town v Southend United |
| Oxford United v Tottenham Hotspur U21 |
| Swansea City U21 v Bristol Rovers |
| Checkatrade Trophy Second Round – North |
| Shrewsbury Town v Walsall |
| Sunderland v Notts County |
| Rochdale v Oldham Athletic |
| Accrington Stanley v Lincoln City |
| Newcastle United U21 v Macclesfield Town |
| Mansfield Town v Bury |
| Port Vale v Stoke City U21 |
| Barnsley v Manchester City U21 |