Following a 6-0 win over Plymouth in the opening round, Pompey will host Mansfield in the second stage of the EFL Football Manager Cup.
The tie will take place on Thursday (April 30) and be available to watch on Twitch.
Managed by supporter – and Football Manager content creator – Jamie King, Mansfield also played saw off Northampton 2-0 to progress.
Following Pompey's 6-0 demolition of Plymouth, manager Proudie said: "I couldn't fault the lads at all today.
"I told the team we were going to attack from the first whistle and they've made me a proud manager.
"I think a few teams in this tournament will look at this result and start worrying about us. I'd back us against anyone."
As well as supporting the Blues during the tournament, you can show your support for the EFL’s charity partner, Mind, the mental health charity.
In these tough times, their services are needed more than ever, so while you’re being entertained by the action, please consider donating on this JustGiving page during the tournament.