Looking Back Through The Decades: Chesterfield In The EFL Cup
07.08.26, 11:32 Updated 07.08.26, 15:25 7 Minute Read
Matthew Rhodes
It's fair to say that Chesterfield doesn't have the best of records when it comes to the EFL Cup. As has been well documented, it's been 20 years since the Spireites even won a game in the competition. Since the EFL Cup first began in the 1960/61 season, the furthest Chesterfield have gone in the tournament has been two trips to the fourth round (last 16). These two cup runs occurred back in the 1964/65 and 2006/07 campaigns.
To whet the appetite further ahead of Chesterfield's trip to Fleetwood Town tomorrow in the first round of this year's competition, let's take a look at the most notable Spireites EFL Cup game throughout each decade since the competition first started.
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Matthew Rhodes Matthew Rhodes is a freelance sports journalist, broadcaster, commentator and author. He was born and raised in Chesterfield and worked as North Derbyshire Radio's senior sports editor from 2021 to 2025. In 2026, his first full-length book was published; 'A Fine Line' covers Chesterfield's astonishing FA Cup run during the 1996/97 season.