In May 2018, friendlies with Folkestone Invicta, Faversham Town, Margate, Tonbridge Angels and Eastleigh were announced.

[46][47] The first round draw was made live on BBC by Dennis Wise and Dion Dublin on 22 October.

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

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

[50] The fourth round draw was made live on BBC by Robbie Keane and Carl Ikeme from Wolverhampton on 7 January 2019.