Shrewsbury Town announced their first pre-season matches on 4 June 2018, with away trips to local rivals AFC Telford United and Port Vale.

[75] The club's pre-season schedule was completed with an away fixture at Bristol City,[76] and matches against Kidderminster Harriers and Burnley to be played behind closed doors.

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

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

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