The Spireites will face Huddersfield Town at the Proact Stadium in the first round of the Capital One Cup.
Mark Robins' side finished the 2013/14 Championship campaign in 17th place, just below Yorkshire rivals Sheffield Wednesday and Leeds United.
Chesterfield last encountered the Terriers in a pre-season friendly ahead of the 2013/14 campaign where goals from Gary Roberts and Jamie Devitt sealed a 2-1 victory for the Spireites.
In March 2012, Huddersfield were victorious in the sides' most recent competitive fixture - winning 2-0 in a League 1 clash at the Proact Stadium through goals from Lee Novak and Jordan Rhodes.
The first round draw was seeded based on the final league positions of teams in the 2013/14 season, and then split regionally between north and south. The Terriers were one of 17 sides that Chesterfield could have drawn from the 'seeds - north' category.
Paul Cook's side faced Leeds United at Elland Road in the first round of last season's competition and narrowly lost 2-1 despite taking an early lead through Eoin Doyle.
All first round ties will be played on the week commencing Monday, August 11. Supporters will be updated with dates and ticket information in due course.
Capital One, the credit card provider and League Cup sponsor has teamed up with all 72 Football League clubs to launch a great offer, where adult fans can buy up to five children’s tickets for just £1 each at all Round 1 matches.
The Capital One website will soon be updated with full details on how to redeem the offer. In the meantime, for any further information please contact your local Football League club or visit www.facebook.com/capitalone