2018–19 Portsmouth F.C. season

The 2018–19 season was Portsmouth's second season in EFL League One. Along with competing in League One, the club also participated in the FA Cup, EFL Cup and EFL Trophy. The season covered the period from 1 July 2018 to 30 June 2019.

Statistics
!colspan=14|Player(s) out on loan:

!colspan=14|Player(s) who have left the club:


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Friendlies
Portsmouth announced they will face Cork City, Havant & Waterlooville, Stevenage, Swindon Town and FC Utrecht as part of the pre-season preparations.

Matches
On 21 June 2018, the League One fixtures for the forthcoming season were announced.

FA Cup
The first round draw was made live on BBC by Dennis Wise and Dion Dublin on 22 October. The draw for the second round was made live on BBC and BT by Mark Schwarzer and Glenn Murray on 12 November. The third round draw was made live on BBC by Ruud Gullit and Paul Ince from Stamford Bridge on 3 December 2018. The fourth round draw was made live on BBC by Robbie Keane and Carl Ikeme from Wolverhampton on 7 January 2019.

EFL Cup
On 15 June 2018, the draw for the first round was made in Vietnam.

EFL Trophy
On 13 July 2018, the initial group stage draw bar the U21 invited clubs was announced. The draw for the second round was made live on Talksport by Leon Britton and Steve Claridge on 16 November. On 8 December, the third round draw was drawn by Alan McInally and Matt Le Tissier on Soccer Saturday. The Quarter-final draw was made conducted on Sky Sports by Don Goodman and Thomas Frank on 10 January 2019. The draw for the semi-finals took place on 25 January live on Talksport.