The young Spireites beat their Shrewsbury Town counterparts 4-2 in a penalty shoot-out after the two teams were locked at 2-2 after extra-time in their FA Youth Cup tie.
Played in wintery conditions at Alfreton Town’ Impact Arena, Chesterfield threatened early on when a Smith cross just evaded Pawson.
Brassey then had a shot saved and Gill almost pounced on the rebound.
Brassey was in the thick of the action again when he set up Ward whose effort was saved.
Spireites keeper Everest Wilcock was called into action during the first 45 minutes, making a couple of saves.
The opening goal came when Everest Wilock used an outstretched leg to make a good save from Thompson and Hughes (67) followed up to score.
Elliott was proving to be a thorn in Shrewsbury’s side after coming on in place of Ward.
Chesterfield levelled when Stringer did well out wide and found Elliott (80) who found the net with a superb turn and finish.
Elliott’s flick-on towards the end of normal time found Pucci but he failed to get his effort on target.
The Spireites went ahead in extra-time when Elliott won a penalty, which was scored by Pawson (94).
Elliott put Stringer through on goal towards the end of extra-time but his effort was saved.
With virtually the last kick of the game, McKenzie-Thompson equalised with a toe-poke following a corner.
Everest Wilcock made two saves in the shoot-out with Wainman, Pucci, Stringer and White hitting the target from the spot.
The young Spireites will travel to Cardiff City in the next round of the competition.
Spireites: Everest Wilcock, Smith (White), Wainman, Ward (Elliott), Bointon, Whitney, Brassey (Stringer), McKernan, Pawson (Weaver), Reah, Gill (Pucci)
