Goalkeeper Cameron Mason was the hero as Chesterfield rose to the challenge of Chester, beating them 5-4 on penalties.
The arrival of winter was clear at the Deva stadium on Thursday night as both sets of fans wrapped up warm for the opening round of the FA Cup Youth as Chesterfield edged past Chester.
The game started with the Spireites dominating as they maintained a high tempo throughout the first half. However, the youngsters were unable to capitalise on their wealth of possession with shots from Mason Coy and James McNicholas just missing the target.
In the latter stages of the first half, Chester battled their way back into the game forcing the Chesterfield defence into some smart blocks and clearances. Mason had to remain focused as he saved from a header with five minutes of the first half to go.
At the half time whistle it was Chester City Youth 0 - 0 Chesterfield Youth but Chesterfield would have been the happier team as they made their way to the dug out.
The second half started the same as the first half as Chesterfield piled on the pressure with good runs from winger Ben Partridge and striker Fabian Johnson panicking the opposing defence. But it was defender Regan Edridge that finally provided a breakthrough for the Spireites slotting home after Chester were unable to clear a loose ball in their penalty area.
Chester levelled just moments later as striker Tom Peers rounded the 'keeper and calmly tapped it home.
The game remained 1-1 and went into extra time.
Penalties seemed imminent throughout an extra time period that saw few chances and no goals with the ball appearing to spend more time in the air than on the grass.
The home fans found their voice towards the end of the game urging their team on and making themselves heard as each player stepped up to take their penalty.
The crowd didn't appear to phase anybody as neither team had missed after the first eight spot-kicks. Chesterfield captain Lawrence Maguire then stepped up and sent the keeper the wrong way to make it 5-4 to the Spireites.
Mason then collected the ball and rolled it to Chester left back Tom Batten. He opted to place the ball into the bottom left hand corner but saw his effort palmed around the post by the Chesterfield stopper.
Youth team coach Mark Smith said “We were allowed to play because they dropped off us, sometimes we over elaborated on the passing which could have been quicker but I do think we had a weapon with the diagonal passes that were being pinged out.”
He added “I think at the end of the day it was a fair result but it's a little bit nerve-racking when you have to do it that way.”