Jason Walker's wonder goal in the dying seconds prevented the Spireites from clinching their first league win of the season at a sun-drenched Bootham Crescent on a beautiful September afternoon, as he met captain Chris Smith's header in the fourth minute of stoppage time to volley home a stunning late equaliser for the Minstermen.
Tommy Wright's side took the lead 10 minutes before the break, when skipper Sam Hird stabbed home his first goal in over three years after Marc Richards was twice foiled by City stopper Michael Ingham, but the home side hit back straight away via Michael Coulson's cheeky lob. Craig Westcarr bagged his second goal in as many outings in the 41st minute when he raced clear from Sam Togwell's ball, but the Spireites' hearts were broken deep into stoppage time when Walker popped up to slam home past a despairing Richard O'Donnell.
Caretaker manager Wright plumped to make four changes from the side that turned over Paul Dickov's Oldham Athletic in the opening round of the Johnstone's Paint Trophy on Tuesday night, with O'Donnell making his first competitive bow between the sticks for the Spireites at the expense of the injured Tommy Lee. The back-four remained unchanged, but 33-year-old Mark Allott replaced Mark Randall in the heart of midfield and youngster Jacob Hazel came in for the injured Danny Whitaker after briefly featuring against the Latics.
Westcarr - who opened his account with a delightful volley before later being dismissed for two bookable offences at Priestfield - returned to the fray following his suspension alongside Richards instead of Scott Boden, who dropped to the bench. 43-year-old assistant manager Mark Crossley was also named amongst the substitutes, with youth prospect Josh Barrington also out injured.
Chesterfield once again lined up in their gold change strip, echoing the shimmering autumnal sunshine that was beating down on a packed Bootham Crescent and once a minute's silence to mark the 22nd anniversary of David Longhurst - who tragically died on the pitch for the Minstermen against Lincoln City - had been impeccably observed, the game got underway.
The Spireites would have been forgiven for thinking Lady Luck was finally on their side after Matt Smith's last gasp own goal for Oldham in midweek and they were almost fortunate to open the scoring early on when Drew Talbot's menacing cross took a deflection before planting the face of the crossbar. The visitors had settled well in the opening exchanges, limiting the hosts to a a couple of harmless corners and with the majority of play being in the City half.
It looked as though a set-piece was the most likely route to goal for Gary Mills' side and they called the previously untroubled O'Donnell into action midway through the first-half, when the former Sheffield Wednesday stopper had to be alert to tip Chris Smith's downward header over. The visitors responded with a smattering of pressure of their own, before O'Donnell collected Walker's tame effort with consummate ease.
The Spireites' plan to press York high up the pitch was working well in the soaring temperature, with Allott in particular catching Daniel Parslow in possession on a couple of occasions with Westcarr unfortunate not to thread Richards through when he had sprung Clarke Carlisle's offside trap. But the former Magpies man was instrumental in the visitors snatching the lead their recent pressure had merited, when his sumptuous dead ball led to Hird's first goal in Chesterfield colours.
Richards has cut a frustrated figure since his arrival in the summer from Port Vale, having been unfortunate not to open his own account for the season on several occasions but he met Westcarr's free-kick with a powerful head before he was denied for the second time by the reflexes of Ingham. He must have been left wondering what he has to do to score, but instead he refused to give up and his persistence paid off when he eventually found Hird for the former Doncaster man to prod home from inside the six-yard box.
It proved to spring what had been a fairly uneventful game into life, as the home side hit back just four minutes later. Coulson had already seen his delightful free-kick superbly beaten away by O'Donnell since the hosts had fallen behind but he was not to be thwarted for a second time and equalised with an audacious chip that left the Town keeper with no chance.
But remarkably, the Minstermen's lead would last just two minutes when Westcarr himself had his second in as many outings. It was courtesy of Togwell's incisive through-ball, which caught out Lanre Oyebanjo and City skipper Chris Smith to enable the 27-year-old to race clear and confidently slot home. The old cliche claims you're at your most vulnerable when you have just scored and that had been proven true twice in quick succession at the Crescent, but the hosts were fortunate not to have conceded again when academy prospect Hazel found space on the far side, but he lashed his effort just wide.
Wright was left with a conundrum as his side faced the second period, whether to try and sit on the lead and invite the home side forward or instead seek a killer goal to put the game to bed and risk being caught on the break. The former is always a dangerous strategy, particularly away from home, and the Scotsman would have been delighted after his side survived a barrage of ariel pressure after the restart.
With legs now weary, Hazel made way for Boden and Westcarr dropped into midfield as the Spireites attempted to catch York cold with the youngster's pace in behind. But it was the lightening pace of City winger Ashley Chambers at the other end which forced Neal Trotman in to a brave block to preserve the visitors' lead. Predictably, the hosts were throwing everything Wright's side and Carlisle came close to squaring things up when he got up to head at goal, but could only nod it the wrong side of the post with Liam Ridehalgh in close company.
At the other end, former Oldham centre-half Trotman forced a smart save from Ingham, although he was pulled up by referee Mr. Darren Bond for an apparent infringement. York boss Mills rang the changes, as the game ebbed away from his team before Wright introduced Craig Clay for Allott and Jack Lester for Richards, who had worked tirelessly throughout the contest once again without a goal to show for his constant toil and endeavour.
The Spireites had to survive a scare late on, as four minutes of stoppage time was displayed on the fourth official's board, when Trotman put O'Donnell in a pickle with an awkward back-pass, but the young keeper acrobatically scissor-kicked the ball to safety before Walker met Chris Smith's header with a wonderful volley to break Chesterfield hearts.
York City (4-4-2) - Ingham; Oyebanjo, Carlisle, C Smith (c), Taylor (Fyfield 64) ; Coulson (78), Parslow, J Smith (Challinor 68), Chambers; Blair, Walker.
Unused Subs - Musselwhite, Bullock, McReady, Potts.
Bookings - Walker (35), Coulson (51)
Goals - Coulson (38) Walker (90+4)
Chesterfield (4-4-2) O'Donnell; Forbes, Trotman, Hird (c), Ridehalgh; Talbot, Allott (Clay 85), Togwell, Hazel (Boden 60); Richards (Lester 88), Westcarr.
Unused Subs - Darikwa, Wafula, Randall, Crossley.
Bookings - Talbot (2), Forbes (56)
Goals - Hird (35) Westcarr (41)
Referee - Mr. Darren Bond
Attendance - 5,119 (1,444 away)