The Spireites have been drawn at against Leeds United at Elland Road in the first round of the Capital One Cup.
The draw was seeded based on the final league positions of teams from the 2012/13 season, and then split regionally - north and south. Chesterfield were grouped in the 'non-seeds - north' category, while Leeds were drawn in the 'seeds - north' category.
The first round of the Capital One Cup will be held on the week commencing Monday, August 5. A specific date and kick-off time is yet to be confirmed.
This will be the first time Chesterfield have faced The Whites since November, 1960 - the Spireites lost 0-4 at Saltergate in the League Cup.
It has been 63 years since Chesterfield have visited Elland Road. Leeds defeated the Spireites 2-0 in the old English Division Two.