2019–20 Portsmouth F.C. season

The 2019–20 season was Portsmouth's third consecutive season in the EFL League One. Along with competing in League One, the club also participate in the FA Cup, EFL Cup and EFL Trophy. The season covers the period from 1 July 2019 to 30 June 2020.

Appearances & goals
!colspan=14|Players out on loan:

!colspan=14|Players who left the club:


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Pre-season and friendlies
On 3 May 2019 Pompey announced their pre-season schedule. A week later a friendly with Stevenage was added.

Matches
On Thursday, 20 June 2019, the EFL League One fixtures were revealed.

FA Cup
The first round draw was made on 21 October 2019. The second round draw was made live on 11 November from Chichester City's stadium, Oaklands Park. The third round draw was made live on BBC Two from Etihad Stadium, Micah Richards and Tony Adams conducted the draw. The fourth round draw was made by Alex Scott and David O'Leary on Monday, 6 January. The draw for the fifth round was made on 27 January 2020, live on The One Show.

EFL Cup
The first round draw was made on 20 June. The second round draw was made on 13 August 2019 following the conclusion of all but one first-round matches. The third round draw was confirmed on 28 August 2019, live on Sky Sports.

EFL Trophy
On 9 July 2019, the pre-determined group stage draw was announced with Invited clubs to be drawn on 12 July 2019. The draw for the second round was made on 16 November 2019 live on Sky Sports. The third round draw was confirmed on 5 December 2019. The semi-final draw was made on Quest by Ian Holloway and Paul Heckingbottom, on 25 January 2020.