
Goals from Ben Thompson, Oli Hawkins, Jamal Lowe and David Wheeler secured victory for the Blues against the non-league side.
The result means the Blues will be in the hat for Monday's second-round draw.
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Here's what fans had to say about Pompey's performance today.
Pete Baldry
Personally I see it as a job well done, but a job that was expected to be done.
Seeing the scorelines that Maidenhead had been losing by over the past few weeks, I would have been expecting a comfortable win.Â
Part of me especially liked seeing the strong side that Kenny put out, shows ambition to hopefully put together a little run in the cup possibly.
Also very happy to see Ben Thompson get his first goal for the club, he will be beyond key for us this season!
Tom Malley
A much improved performance second half. Completely dominated but that should be the case against these teams.
Great to see both loanees Thompson and Wheeler score.
Job done and into the next round.
Tony Boulton
Pretty one sided game. No joy for the underdogs against League One Pompey.
Nice paycheck from TV coverage for the National League team.
Will Hucker
Very pleasing, professional display from Pompey.
Credit to Maidenhead for their first half performance, unfortunate not to score.
Good cup tie, great respect shown to the opposition and the competition by Jackett.
Rob Whyley
Professional display from Pompey today and treated their opponents with respect.
Maidenhead did themselves justice.
Onto the next round. Play up Pompey.
Shawn Woodward
We dominated possession but they had their moments.
Mick Hill
4-0 has to be pretty impressive even if it is away to a lower league.
Richard Price
The first half is always the same against non league. They stack 10 men behind ball and hoof it.
In the second half we controlled it. Was a training routine that last half.
Conrad Jones
Well done Kenny and all the lads.