As of 18 July 2018, Sunderland have announced five pre-season friendlies against Darlington, Hartlepool United, Grimsby Town, St Mirren, and Middlesbrough.

[12] The draw for the second round was made live on BBC and BT by Mark Schwarzer and Glenn Murray on 12 November.

[15] The draw for the second round was made live on Talksport by Leon Britton and Steve Claridge on 16 November.

[16] On 8 December, the third round draw was drawn by Alan McInally and Matt Le Tissier on Soccer Saturday.

[17] The Quarter-final draw was made conducted on Sky Sports by Don Goodman and Thomas Frank on 10 January 2019.