Conor Wilkinson's two goals sandwiched a Kristian Dennis spot-kick as the Spireites came within moments of a win, but conceded late again to draw 3-3
With barely a minute on the clock, Wilkinson continued his goalscoring arrival with a controlled volley from Jon Nolan's sublime left-wing delivery, and after Nolan was fouled in the box just after the break Dennis confidently added a second from 12 yards.
Gillingham pulled one back just past the hour through a contraversial Jay Emmanuel-Thomas penalty, but within ten minutes Wilkinson had restored the two-goal lead and doubled his tally with a lovely lofted finish from close range, before moments later Emmanuel-Thomas scored another penalty before Scott Wagstaff claimed the point with the final touch of the game.
The Spireites took the lead before Gillingham had even touched the ball, Nolan’s curled free kick fell directly at the outstretched foot of Wilkinson, the towering forward had escaped his marker and knocked it into the bottom corner.
The freekick had came after Reece Mitchell took an elbow to the face in the first move of the match, giving the home side an opportunity on the left edge of the penalty area.
Almost too eager for an instant reply, Mark Byrne took possession of the ball in the Spireites half and with just a couple steps forward struck it goalwards and over the bar.
Chesterfield had been under pressure since their equaliser but when Gboly Ariyibi received the ball he sensed a chance and drove upfield, stepping over and passed a defender he whipped the ball into Wilkinson who towered above the defender but glanced the header just wide.
The Gillingham 'keeper would then misjudge a stray ball near the corner flag, Ariyibi got there first but Wilkinson couldn't beat his marker to the resulting low cross.
Clearly buoyed by his goal, Wilkinson collected a pass from Kristian Dennis and turned inside only to be taken down as he looked to strike; he hit the resulting freekick low but straight at the wall.
Receiving the ball on the right of the area once more, Wilkinson fooled his marker and turned inside, this time his crossed landed straight onto the head of Sam Hird who knocked it back into the box, Stuart Nelson flapped but no one could meet it.
With their first real chance of the half, Emmanuel-Thomas met a low cross on the turn but his shot was scuffed and sailed over the ball.
Ariyibi had been looking lively all game and after picking up the ball deep into the Gills' half, he looked up and placed it between the Spireites’ forward pairing, but it was too powerful for either to make contact.
A Chesterfield clearance up field caught the away side off-guard, a Gillingham defender attempted to head it to Nelson, but Mitchell chased it down and was only narrowly beaten by the Gillingham ‘keeper.
Not to be disheartened by his first two ventures outside of the box, Nelson charged forward again to meet another stray ball, this time only just beating Dennis to the ball.
Fuelled by their lack of direct chances, Emmanuel Osadebe took the Gills final attack of the first half himself. The midfielder had driven down the left wing and into the box, he looked into the area, but instead struck it goalwards and past the posts.
The game grew increasingly heated during the second half and when Wilkinson collected the ball on the outside of the area he drove between two Gills defenders.
The defensive duo knocked the goalscorer to the ground, but with the last touch of his toes he found Dennis who was then brought down himself. In the absence of Jay O’Shea, Dennis took the resulting penalty and cooly converted.
The away side were awarded a lifeline in the 63rd minute when Deji Oshilaja fell in the box after meeting a long-ball from the Gillingham defence, the referee awarding a penalty for a shirt pull from Tom Anderson.
Emmanuel-Thomas stepped up, and after a delayed run up struck it into the bottom corner.
Determined to equalise, the away side had pushed everyone forward in only the 70th minute, Ariyibi snatched the ball and sprinted upfield. The winger was tackled but Liam Graham picked up the debris and threaded it through to Wilkinson, the striker lobbing Nelson for his second of the evening.
The drama increased as the Gills were awarded their second penalty of the night, Emmanuel-Thomas had found Wagstaff but debutant Laurence Maguire looked to bring the winger down.
Emmanuel-Thomas was the taker once more, he took the same delayed run up and placed it into the same corner to decrease the Spireites lead to just one goal.
The Spireites were on the defensive with Gillingham in search of a late equaliser, Osadebe found himself free on the left wing but Graham recovered well with a brilliant sliding challenge to save the Spireites.
With five minutes of injury time to come Gillingham flung a desperate cross into the box; confusion between Ryan Fulton and his defence left the goal unmanned, but Gillingham couldn't find the net.
Just as Chesterfield looked set to see the game out, Dack received the ball in the Spireites penalty area, his initial attempted was saved but Wagstaff arrived unmarked to place home the rebound and break Chesterfield hearts
Chesterfield: Fulton (gk) - Maguire (Donohue 86'), Hird, Anderson, Graham - Mitchell (O'Shea 62'), Liddle (c), Nolan, Ariyibi - Wilkinson (Dimaio 77'), Dennis
Subs not used: Parkin (gk), Gardner, Evatt, German
Gillingham: Nelson (gk) (c) - Ehmer, Oshilaja, Wagstaff, Knott (List 59'), Pask, Byrne, Dack, Oldaker, Osadebe, Emmanuel-Thomas
Subs not used: Hadler, Wright, Dickenson, Hessenthaler, Chapman, McDonald
Chesterfield: Wilkinson 2' 72', Dennis 52 (pen)'
Gillingham: Emmanuel-Thomas 65' (pen), 76' (pen), Wagstaff 90+5
Attendance: 4,714 (124 away fans)