The season covers the period from 1 July 2018 to 30 June 2019 Tranmere Rovers announced friendlies with Dunfermline Athletic, Liverpool, Wigan Athletic, Warrington Town, Fleetwood Town, Chorley and Rochdale.

[50][51] The first round draw was made live on BBC by Dennis Wise and Dion Dublin on 22 October.

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

[53] The third round draw was made live on BBC by Ruud Gullit and Paul Ince from Stamford Bridge on 3 December 2018.

[55] On 13 July 2018, the initial group stage draw bar the U21 invited clubs was announced.