The Spireites will host Pompey at the SMH Group Stadium in the first round of the famous competition.
Ahead of the exciting game, we delved into the archives to look back at the last time Town beat Portsmouth.
Here are 13 random pictures from that day, which was 10 years ago in August 2013, when two late goals from Armand Gnanduillet and Tendayi Darikwa handed Paul Cook’s men a memorable victory to send them top of League Two.
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