This coming Wednesday sees the Spireites take on Manchester City U21 in an intriguing Checkatrade Trophy clash at the Proact (7pm).
Chesterfield have a strong chance of qualifying for the next round of the competition, with a victory potentially meaning they top the group. A win on penalties meanwhile will be enough to seal second place.
However despite Man City failing to win a game in normal time in the tournament so far, they will still present a stern test for Jack Lester's side.
The manager of Man City's U21 side is currently Simon Davies, who was a part of the class of 92 at Manchester United. He won the FA Youth Cup in 1992 and went on to play 11 times for the first team. He was also capped by Wales on one occasion.
He went on to feature for Exeter and Huddersfield on loan before also playing for the likes of Luton Town, Macclesfield Town and Rochdale.
Davies hung up his boots in 2007 and went on to manage Chester, before serving as assistant manager to Patrick Vieira in Man City's U21 team from 2013-2015. He then got given the job on a full time basis in 2016. Davies' side currrently reside in 8th place in PL2 Division One
The Man City side could include names who are starting to feature in the first team.
The main player to potentially feature would be Phil Foden who won the U17 World Cup with England and was named the player of the tournament. Foden made his first team debut in the Champions League against Feyenoord this season.
Another member of England's victorious U17 side, Joel Latibeaudiere, could play in defence having started Man City's win on penalties over Rotherham in August.
Spanish midfielder Brahim Diaz may also be in the squad to face the Spireites on Wednesday. The 18-year-old made his first team debut in the EFL Cup last season and has also made one appearance off the bench in the Champions League this campaign.
Tickets for the match are still available, click here to view a full list of prices.