Blues Betting: Crawley (H)2 September 2019
Pompey begin their defence of the Leasing.com Trophy with a group match against Crawley on Tuesday.
Blues Betting: Blackpool (A)29 August 2019
Pompey will look to take their cup form into the league when they visit high-flying Blackpool on Saturday.
Blues Betting: QPR (A)27 August 2019
Pompey switch their attention to trying to progress in the Carabao Cup when they visit QPR on Wednesday evening.
Blues Betting: Coventry (H)19 August 2019
Pompey will look to secure a return to winning ways in League One when they host Coventry on Saturday.
Blues Betting: Sunderland (A)15 August 2019
Pompey make their longest League One journey of the season on Saturday when they visit Sunderland.
Blues Betting: Tranmere (H)8 August 2019
Pompey will look to put their first League One points on the board when they host Tranmere on Saturday.
Blues Betting: Birmingham (H)5 August 2019
Pompey switch their attention to the Carabao Cup when they host Birmingham in Tuesday’s first round tie.
Blues Betting: Shrewsbury (A)1 August 2019
Pompey will look to make a positive start to the 2019/20 campaign when they visit Shrewsbury on Saturday.
Blues Betting: Sunderland (H)14 May 2019
Pompey will try to reach Wembley for a second time this season when they host Sunderland in the second leg of their play-off semi-final.
Blues Betting: Sunderland (A)9 May 2019
Pompey will try to take one step closer to Wembley when they visit Sunderland in the first leg of the play-off semi-finals.
Blues Betting: Accrington (H)2 May 2019
Pompey will look to secure third spot in the table when they host Accrington in the final game of the regular season on Saturday.