The Spireites have drawn Southend United at home in the second round of the 2013/14 FA Cup.
Following Saturday’s 2-0 victory over Daventry Town at the Proact Stadium in the first round of the competition, Chesterfield FC were entered into Sunday afternoon’s draw held at Wembley Stadium.
The Shrimpers beat Morecambe 3-0 in their first round fixture to earn a place in the second round draw.
The game will be played on the weekend of Saturday, December 7 or Sunday, December 8.
Sky Bet League Two rivals Southend, who are in ninth spot, last visited the Proact in August this year, where Chesterfield prevailed in the League Two fixture through a last minute Armand Gnanduillet header.