The youth team were knocked out of the National League Academy Cup on penalties after a 1-1 draw at York City on Thursday afternoon.
There were nine changes made to the team that lost 4-3 to Salford City earlier this week with only Matt Fuertado and Josh Turner keeping their places in the starting line-up.
The first half was a tense affair with both teams doing well to cancel each other out as the sides went into half time goal-less.
Chesterfield changed the system changing from a 4-3-3 to a 3-5-2 – a system that suited the side a lot better. They controlled the game a lot more in the second period and saw a lot of half-chances go begging.
With just three minutes to go, York took the lead through Will Jackson, the midfielder picking the ball up on the edge of the box before firing past Dylan Wharton.
The Spireites pushed forward in search of an equaliser and found it with just a minute to go through Callum Brook.
Regan Hutchinson almost won it in added time when he took the ball round Jake Teal but could only fire wide from an acute angle.
With no extra-time to separate the sides, the game went straight to penalties. Hutchinson and Samuel Geeves scored their spot kicks, but York won the shoot-out 3-2 to knock the Spireites out of the competition.
Despite the loss, coach Neil Cluxton saw the positives from the game to take forward to Saturday’s game against Doncaster Rovers. He said: "We go again on Saturday. It’s back to the bread and butter, back to the league.
“We’ve had a good little run over the past month, so I’m going into the second half of the season with a bit more confidence. Doncaster are second in the league so it’s going to be a tough game, but I’m hoping we can have a good go at them."
Spireites: Wharton, Brook, Gibson, Geeves, Render, Sharman, Tansley, Fuertado, Hutchinson, Turner, Smith.