The Spireites' youth team travel to the King Power Stadium to take on Leicester City in the fourth round of the FA Youth Cup.
The match on, kicking-off at 7pm on Monday evening, comes after the Spireites' incredible comeback to beat Aston Villa 3-2 at the Proact in the third round.
Speaking ahead of the game Academy Director Gerry Carr was looking forward to another big clash against Premier League opposition.
He said: “We’ve been doing our pre-planning since our last game. We had a little disruption last week with our game abandoned after 20 minutes, but our preparations have been similar to the last game against Aston Villa.
“We’ll be going there as huge underdogs but with our lads and the team spirit, we’ll certainly be going there with belief.
“We’ll have our lads filled with confidence and if 11 lads for us play well on the night and Leicester have some lads who have a bit of an off night who knows what’ll happen.
Carr has been proud of the side’s run, and while he wants the players to enjoy the occasion he also expects them to put on a show, with a trip to either Everton or Southampton a reward for the winners.
“It’s no secret that our group’s a lot stronger this year,” he said. “It’s been great so far to progress through three rounds, I’m not sure of the last time the club got to this stage.
“Everything’s been done as meticulously as we can and we’ll certainly let our lads enjoy the night and play with a smile on our faces.”
“We’re playing at a fantastic arena, the lads will remember it for the rest of their lives, and from my perspective as academy manager I just want them to go and put on a good show with maximum effort.
“At the end of the day they’re all representing Chesterfield Football Club. I don’t think Leicester will be taking us lightly because anyone who can beat Aston Villa in the manner that we did will be shown a lot of respect.”