Crewe will travel to the Kit Kat Crescent to take on Blue Square Premiership side York City.
The Minstermen who is managed by former Port Vale boss Martin Foyle sit 6th in the BSP and have yet to lose at home in the league with five wins and four draws and they will provide a difficult game for the Railwaymen.
The two teams have met twice in the FA Cup with the Minstermen winning both 2-1 in 1962 and 3-1 in 1986.
The last time Crewe played York was away in the League Cup back in 2001 where that day Crewe won 6-5 on penalties after drawing 2-2 after extra time.