2018–19 Southend United F.C. season

The 2018–19 season was Southend United's 113th year in existence and their fourth consecutive season in League One. Along with competing in League One, the club participated in the FA Cup, EFL Cup and EFL Trophy.

The season covers the period from 1 July 2018 to 30 June 2019.

Friendlies
Pre-season friendlies with Great Wakering Rovers and Leyton Orient were announced on 21 May 2018.

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.

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.