It took an extra 30 minutes seperate the sides at the Proact, but coming from behind Carlisle United eventually prevailed 2-1 in the FA Youth Cup second round.
A goal-less first half gave way to a more attacking second. Jack Egan cracked the bar for the Cumbrians after the break but the Spireites went ahead thanks to a brilliant Dylan Hand freekick.
However, Egan took the game to extra time when he levelled matters five minutes from time with a smart ten-yard finish. In the extra 30 minutes, George Clarey struck the post for the hosts before Max Cowburn won the tie for Carlisle with a strike inside the area.
The home side dominated the opening minutes, the first chance of the game fell to Joe Rowley. After linking well with Ricky German, his angled shot was blocked at the near post. From the resulting corner Rowley fizzed a ball across the face of goal, just out of the reach of the Spireites attackers.
Carlisle responded well, Cameron Salkeld tested Dylan Parkin from just inside the box but his strike lacked the power to trouble the goalkeeper low down to his left.
With 25 minutes gone German swung a high ball to the back stick, it fell kindly to Rowley but his snapshot was straight at Morgan Bacon in the United goal. Minutes later at the opposite end Salkeld saw a downward header slide the wrong side of the upright with Parkin scrambling.
As the half drew to a close German latched on to a Ify Ofoegbu through ball, muscled his way past Joe Breen but could only find the palms of Bacon. Seconds later Tipping glanced an Owen Darwent's cross inches wide of Bacon’s back post.
The final chance of the half - dominated by the blues - fell to the lively German whose curling effort narrowly missed the top corner and the teams went in level at the break.
The second half started at a frenetic pace with chances at both ends. Cowburn forced Parkin in to a smart save in the Spireites goal and then Rowley saw an effort blocked by Dean Watson after German’s neat cutback.
Egan rattled the crossbar for the Cumbrians with a rasping drive from the corner of the 18-yard box. The ball sat up nicely for the winger whose superb effort beat Parkin but rebounded to safety off the underside of the bar.
Moments later German again found himself bearing down on Bacon’s goal but again the Carlisle’s number one was equal to the striker's effort. From the resulting corner, substitute George Lynam had a powerful header cleared off the line.
The deadlock was finally broken on 74 minutes via a sublime Hand free kick. The Chesterfield midfielder curled a beautiful free kick over the Carlisle wall and into the right hand top corner leaving Bacon with no chance.
But the lead didn't last long. Just nine minutes later a deep free kick dropped invitingly to an unmarked Egan who slotted home from 12 yards bringing the visitors level. It proved to be the final action of the 90 minutes.
The first chance of extra time fell to German who saw his effort blocked by the Carlisle right-back, that was quickly followed by a golden opportunity for George Clarey. The second-half substitute skipped passed the on-rushing Bacon but fired his angled shot against the upright.
Eight minutes into extra time Carlisle grabbed the lead. Cowburn rose highest on the six-yard line to power a header passed the left hand of Parkin.
Clarey had a golden opportunity to bring the Spireites level minutes into the second half of extra time when he beat Bacon to a through-ball but couldn't find the target with the goal gaping.
Parkin was then called in to action making a superb double save to keep his side in the tie.
At the other end his opposite number Bacon excelled himself again, denying German on two occasions. The last chance of the game went the way of the Spireites but Connor Fowler couldn't keep his volleyed effort down.
Chesterfield: Parkin (gk) - Ofoegbu, Fowler, Taylor (Sennett-Neilson 69'), Hand, Smith, Darwent (Lynam 57'), Rowley, Tipping (Clarey 82'), German, Wakefield
Subs not used: Jones, McKenna
Carlisle United: Bacon (gk) - Olson, Brockbank (Goldthorpe 108'), Watson (Kelly 105'), Taylor, Breen, Cowburn, Holt, Salkeld, Dixon (Lloyd 63'), Egan
Subs not used: Hall, Ashton
Chesterfield: Hand 74'
Carlisle United: Egan 85', Cowburn 102'