Paul Benson's diving header deep in to stoppage time all but ended Chesterfield's hopes of creeping into the League Two play-off places as the former Swindon Town marksman headed home Billy Jones' cross to give the home side a hugely undeserved three points at Whaddon Road on Tuesday evening.
The 33-year-old pounced in the 92nd minute with virtually the hosts' first meaningful assault on Tommy Lee's goal to dispatch a sickening smash and grab winner to send the Robins into third place and keep the Spireites 11 points adrift of seventh, as Chesterfield's season was encapsulated in 60 disastrous seconds.
Paul Cook took his side to Whaddon Road following a hard-fought 1-0 win against Dagenham & Redbridge at Victoria Road on Saturday, courtesy of Daggers skipper Abu Agogo's 19th minute own goal. The victory was enough to give the Spireites only their fourth win in 14 outings since their last away win against promotion chasing Port Vale in early December and put an end to over 270 minutes without finding the net after a barren spell in front of goal.
The win in Essex also kept Chesterfield's faint play-off hopes still alive, mathematically at least, with the Spireites trailing local rivals Rotherham United by 10 points in spite of languishing down in 14th place. Cheltenham, meanwhile, went into the game following a remarkable run that has seen them suffer just three defeats in their last 17 league games after they were heavily beaten 4-1 at the Proact in late November.
The Robins remained unbeaten in their last five and Mark Yates' side got their automatic promotion chances back on track after a 2-1 home win over resurgent AFC Wimbledon on Saturday. With a trip to the Pirelli Stadium on the horizon for the Gloucestershire side, a win for the hosts would see them leapfrog Burton Albion into the third and final promotion spot. Cook plumped to name an unchanged side from the one that edged past Wayne Burnett's side on Saturday in spite of not making any substitutions in the capital, but top goalscorer Jack Lester returned to the bench after recovering from a virus alongside Tendayi Darikwa who has completed his recovery from a hernia operation.
With the game having been moved to a Tuesday night due to next week's Cheltenham Festival it was the hosts who got out of the traps quickly and hit the ground running through Darren Carter, but the former Sunderland midfielder could only curl his effort from the edge of the box into the waiting arms of Lee after some neat footwork from Sam Deering. The lively 22-year-old broke down the right flank soon after and following Liam Cooper's superb intervention, Keith Lowe somehow missed a free header from barely six yards from the ensuing corner.
It was a huge let off for the visitors and they made their first assault on the Town goal in the 11th minute after skipper Sam Hird found Jay O'Shea on the right and after the Irishman had exchanged passes with right-back Drew Talbot, he horribly miscued his attempt wide with his weaker foot. Neither side had been able to assert themselves during the opening 15 minutes but the Spireites, once again in their gold change strip, gave Town keeper Scott Brown a fright midway through the first half when the unpredictable Ivorian Armand Gnanduillet did superbly well to chest the ball down and unleash a ferocious drive from 20-yards that the former Bristol City stopper had to be alert to gather at his near-post.
It was an encouraging sign for the Liverpudlian with his side having shipped just four goals in their previous eight games and with the game drifting towards the half-hour mark, the hosts were forced to withstand a barrage of crosses as Chesterfield peppered the Town goalmouth. Gnanduillet was once again proving a handful, but the former Le Havre man very much remains a raw talent and he should have certainly given the Spireites the lead when he expertly peeled away from Jason Taylor, but he could only head O'Shea's inviting cross into the ground.
Cook's side were visibly growing in confidence and buoyed by his strike against Dagenham, or at least the one he tried to claim, Sam Togwell attempted to repeat the feat from 30-yards but after a nasty bobble he almost shanked his drive out of the ground like a horribly timed tee shot into the rough. O'Shea was the next to send another wayward drive into orbit six minutes before the break, while at the other end a couple of superbly-timed sliding challenges from Cooper thwarted Paul Benson.
Just as he had done all season so far, 30-year-old striker Marc Richards had worked tirelessly up front without reward and he was unfortunate not to break the deadlock when his attempted drive took a deflection off Steve Elliott en route and Conor Townsend flashed a header narrowly wide of the upright following another deep cross towards the far post, but as the whistle blew for half-time the game remain delicately poised with the visitors unable to turn their dominance into goals.
As things stood at the break, a win for the visitors would propel them back into 10th place and eight points behind Northampton Town in the final play-off place and Gnanduillet came close to picking out strike-partner Richards after embarking on a solo run following the restart. O'Shea was next to send a teasing ball across the face of goal, but it eluded everyone in the six-yard box including on loan Hull winger Townsend who was creeping in at the far post.
The second period had resumed normal service, but the visitors remained toothless in the final third with Gnanduillet again coming close when he rolled Elliott but his attempted drive was deflected over. Remarkably, the Spireites are yet to be awarded a penalty in the league this season - currently the longest run in English football without a spot-kick - and yet again they were harshly done by when Hird's attempted cross appeared to strike an arm in red and white, but referee Mr. Andy Woolmer denied ambitious appeals from the 100 or so away fans behind the goal.
Richards' frustrations were beginning to show on the hour mark when he was booked for preventing a quick free-kick from being taken and with Cook's side urgently requiring a goal, the gaffer turned to evergreen striker Lester to replace the former Port Vale man. The 37-year-old almost had the fairytale introduction too, when he swivelled to fire a left-footed drive over after Togwell had managed to turn O'Shea's centre back into the box.
Yates' answer was to introduce the pacy Jermaine McGlashan in an attempt to open the game up, but once again it was the visors on the offensive when O'Shea teed up Hird but his pile-driver was blocked. Nathan Smith, who had been impressive again at left-back, was then booked 16 minutes from time after wrestling McGlashan to the ground when he had flown past him and Jason Taylor was inches away from snatching an undeserved opener when he sent a vicious volley inches over the crossbar.
Darikwa was the next to step off the bench, replacing Gnanduillet 10 minutes from time with O'Shea shuffling inside, but it was Lester who was inches away from winning it five minutes from time when he wriggled away from Elliott to find an inch of space and fire a powerful drive just the wrong side of the post. Both sides now had the finishing post firmly in their sights and were giving it one last crack of the whip as three minutes of additional time was indicated, but as so often has been the story this season, the Spireites were unsurprisingly punished as Benson headed home an unstoppable diving header to give a the Robins all three points with their first shot on target of the entire contest.
Chesterfield (4-4-2) - Lee, Talbot, Trotman, Cooper, Smith; O'Shea, Hird (c), Togwell, Townsend; Gnanduillet (Darikwa 80), Richards (Lester 61).
Subs not used - Barrington, Whitaker, Brindley, Randall, Clark.
Bookings - Richards (61), Smith (74)
Goals - N/A
Cheltenham Town - Brown; Lowe, Elliott, Taylor, Jones; Penn (c) (McGlashan 64), Carter (Harrison 64), Deering (Mohamaed 85), Pack; Benson, Hector.
Subs not used - Roberts, Duffy, Harrad, Jombati.
Bookings - N/A
Goals - Benson (90+2)
Referee - Mr. Andy Woolmer
Attendance - 2, 195 (125 away)