Pompey will play Aston Villa U21s in the group stages of the 2022/23 Papa John's Trophy.
The Premier League side's youngsters were drawn into Southern Group B, which already contained the Blues and League Two duo AFC Wimbledon and Crawley.
Pompey will take on the Villans and one of the other clubs at Fratton Park, while also having one away fixture as they battle for a place in the knock-out stages.
Kenny Jackett guided the Blues to EFL Trophy glory with a memorable penalty shoot-out victory over Sunderland in 2019.
But the Blues were defeated by Salford in the delayed 2020 showpiece and went out in the third round last term.
|Southern Group A||Southern Group B||Southern Group C||Southern Group D|
|Brighton U21||Aston Villa U21||West Ham U21||Tottenham U21|
|Southern Group E||Southern Group F||Southern Group G||Southern Group H|
|Plymouth||Forest Green||Leyton Orient||Ipswich|
|Crystal Palace U21||Southampton U21||Chelsea U21||Arsenal U21|
|Northern Group A||Northern Group B||Northern Group C||Northern Group D|
|Everton U21||Leeds U21||Wolves U21||Liverpool U21|
|Northern Group E||Northern Group F||Northern Group G||Northern Group H|
|Newcastle U21||Man City U21||Man United U21||Leicester U21|