The young Spireites were cruelly knocked out of the FA Youth Cup by Hereford United through a late goal in the dying minutes of additional time.
Dylan Bonella scored with practically the last kick of the game to send the Bulls through to the third round of the cup and stop Chesterfield at the second round.
The game started brightly but neither side could maintain possession as they were both playing with a direct style and looked to get forward wherever possible.
Chesterfield enjoyed the first opportunity of the game through Joe Massey as the ball broke for him on the edge of the Hereford area. However, his looped half volley was slightly overhit and went over Kyle Moore's crossbar.
The Spireites continued to press and a deep corner was delivered to Regan Edridge storming into the box at the back post. The defender's header back into the six-yard box was met by Fabien Johnson who just couldn't get enough on the ball to direct it into the Bulls goal.
Johnson was involved again a matter of minutes later; he found space on the left wing and latched onto a lofted pass, beating the Hereford 'keeper to the ball who had stormed off his line. The striker composed himself and attempted to finish past Moore but the goalkeeper stood his ground well and saved Johnson's effort.
Spireites 'keeper Cameron Mason was called into action for the first time as the game approached the half hour mark, throwing himself to his left hand side to spectacularly save a long range Hereford effort.
Chesterfield next went close when Ben Partridge broke free from midfield and advanced on the Bulls goal, taking his time before unleashing a powerful shot from just outside the area that was well saved by Moore.
The sides tussled for possession as the first half came to a close but neither could create a clear cut opportunity and went into the break level.
Chesterfield earned the first opportunity of the second half as they broke through Jake Beesley, the forward then found Alex Hewitt on the right wing who crossed to Luke Randle at the back post but the full-back's effort wasn't strong enough to trouble the Bulls 'keeper.
That was to be Beesley's final contribution of the game as he was replaced by Jordan Walshaw just before the hour mark.
Walshaw was involved in the action straight away, getting on the end of a Oliver Brock diagonal ball to the left wing. The striker then beat his marker before firing a shot at Moore from a tight angle, the Bulls 'keeper did well to charge to shot down and clear it to safety.
Hereford struggled to get a foothold in the second half and were unable to create an opportunity until 20 minutes in when Billy Murphy found a yard of space on the edge of the Chesterfield area before shooting well over Mason's goal.
The Bulls enjoyed the best opportunity of the game soon after as Cory Williams broke clear of a Jamie McNicholas challenge and had only Mason to beat but his low right-footed effort fizzed past the Spireites post.
McNicholas was involved again almost instantly as Mason punched a cross to the edge of the Spireites area for Bonella to strike first time but the defender got back brilliantly to get in the way of the shot and head clear.
The Herefordshire side began to press the Spireites and missed another guilt-edged opportunity as the ball broke for Williams inside the Chesterfield area but the Bulls striker could only drag his shot wide.
As the game neared the 90-minute mark Ben Partridge broke down the right wing and into the Hereford area before crossing to the outside of the area for Lewis Sugden whose first time effort fell wide of Moore's post.
Spireites hearts were broken in added time as a speculative long range Bonella effort struck the inside of Mason's post and hit the back of the net to the delight of the travelling support.
The goal was near enough the last kick of the game as Chesterfield barely had enough time to get the game back underway before the final whistle was blown.
Chesterfield: C Mason, J Massey, L Randall, O Brock, R Edridge, J McNicholas, B Partridge, L Sugden, F Johnson (C Morrison 88'), A Hewitt, J Beesley (J Walshaw 55').
Subs not used: J Bayne, J McCready, J Hudson.
Hereford United: K Moore, A O'Kelly, C Saunders, B Murphy, J Gregory, M Kontic, B Miller, C Brennan, C Williams, D Bonella, T Brock.
Subs not used: M James, M Burgess, W Haines, L Fletcher, C Clarke.
Goals: Chesterfield 0 - 1 Hereford United (D Bonella 90+2')