Friendlies against St Mirren, Atherton Collieries, FC Halifax Town, Morecambe, Girona, Guiseley and Peterborough United were confirmed.

[1] The game against St Mirren was cancelled a day before when the players went on strike due to unpaid wages.

[6][7] Bolton began their league campaign at newly relegated West Bromwich Albion on August 4 and finished it away at Nottingham Forest on May 5.

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

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