Up Notes: On 15 June 2019, The Cumbrians announced their pre-season schedule.

Source: BBC On Thursday, 20 June 2019, the EFL League Two fixtures were revealed.

[10] The second round draw was made live on 11 November from Chichester City's stadium, Oaklands Park.

[11] The third round draw was made live on BBC Two from Etihad Stadium, where Micah Richards and Tony Adams conducted the draw.

[13] The second round draw was made on 13 August 2019 following the conclusion of all but one first-round matches.