Pompey have been drawn at home to League Two side Stevenage in the last 16 of the Papa Johns Trophy.
The tie is scheduled to take place at Fratton Park in the week commencing December 12.
It will be the first meeting between the sides since an opening round tie in the League Cup back in August 2020.
Stevenage's path to this stage of the competition saw them finish above Peterborough to top Southern Group D.
Steve Evans' side then enjoyed a 3-2 victory over Arsenal U21s on home soil on Tuesday night.
The Boro are currently sitting second in the League Two table and visit King's Lynn in the FA Cup this weekend.
| Papa Johns Trophy Round of 16 – Southern Section |
| POMPEY v Stevenage |
| Cheltenham Town v Chelsea U21 |
| Bristol Rovers v Milton Keynes Dons |
| Plymouth Argyle v AFC Wimbledon |
| Papa Johns Trophy Round of 16 – Northern Section |
| Salford City v Port Vale |
| Bolton Wanderers v Manchester United U21 |
| Lincoln City v Everton U21 or Mansfield Town |
| Burton Albion v Accrington Stanley |