The first half was a particularly even affair with Deering causing numerous problems for the visitors while O'Shea looked dangerous putting balls into the Cheltenham box.
The visitor's enjoyed the majority of the second half but were unable to create any clear-cut chances on goal. Then in the 91st minute, Paul Benson got on the end of a Billy Jones cross to move Cheltenham into the third automatic promotion place in npower league two.
Both sides started the match with the same starting eleven that won on the weekend. Steve Elliott and Darren Carter both recovered from knocks on Saturday to be selected for tonight's game. Jack Lester rejoined the Chesterfield squad claiming a space on the bench after missing their 1-0 win against Dagenham and Redbridge with a virus.
Prior to the game Cheltenham had an appalling record against today's visitors but the Robins were buoyed by a 2-1 victory over Wimbledon on Saturday. Mark Yates felt that psychologically that win would have been massive for them and it showed as Paul Benson's goal was their first against the Spireites at home in 7 attempts.
A beautiful day transformed into a chilly evening under the floodlights and a clear sky at the Abbey Business Stadium. The Robins started the brightest, Sam Deering's tricky footwork earned the midfielder space on the edge of the box. He lay the ball off to Carter who could only curl his left footed strike into the arms of Spireites shot stopper Tommy Lee.
The midfielder was involved again shortly after. Deering's pace helped win a corner when his cross was blocked by the Chesterfield defence. Keith Lowe connected with the resulting set-piece but could only head his effort high over the crossbar.
Deering caused problems for Chesterfield for much of the half, popping up in all area's of Whaddon Road, running at the opponents defence and putting crosses into the box that unfortunately came to nothing.
Chesterfield's main style of play had been trying to put long balls over the top of Cheltenham's defence. The Cheltenham back four dealt with that tactic with relative ease and their guests first chance fell midway through the half, Gnanduillet received the ball on the right hand side from a throw in and showed the threat he possesses by firing a powerful shot goal-bound that was comfortably saved by Scott Brown.
The visitor's best chance of the game again came from the right flank. O'shea's cross found an unmarked Gnanduillet who could only bounce his free header into the ground. The striker will undoubtedly feel he should have done better.
More slick passing in possession for the Robins earned them another chance in attack. Neat play in the right channel enabled the ball to find the feet of Jason Taylor on the edge of the box. He was allowed time to turn by the visiting defence but his weak shot failed to test Tommy Lee in the Spireites goal.
It was Chesterfield ended the half the brighter though. First, Togwell's deflected shot was easily collected before Townsend will have wished he'd done better just moments before the break. Richards, Togwell and O'Shea all linked up well before another dangerous O'Shea cross this time found Conor Townsend whose headed effort failed to test Scott Brown, glancing wide past the left upright.
Half Time: Cheltenham Town 0-0 Chesterfield
Darren Carter couldn't make the most of the Robins first chance in the second half. Advancing into the penalty area the midfielder managed to get a shot away under pressure but couldn't direct his shot on target.
From then, it was the visitors that most of the half.
Chesterfield were looking much more dangerous having ditched their long ball syle of play from the first half. They were teasing the away fans behind the goal they faced by whipping crosses across the face of goal, falling inches in front of onrushing attackers.
The Spireites passing play was forcing numerous errors in the Robins defence. A mistake by Elliott unleashed Jay O'shea who fed Gnanduillet who's deflected shot resulted in a tame corner that came to nothhing. The Robins were struggling to regain control of the game and a double substitution from Mark Yates signalled a change in formation. Harrison and McGlashan replaced Carter and Penn as they lined up 4-4-2.
McGlashan made an immediate impact. Running with more pace than Deering could manage on the right flank and earning a corner early on but again Chesterfield rallied. Veteran striker Jack Lester showed his quality shortly after joining the action. He knocked the ball down on his chest but could only fire his volley left footed over the bar from the edge of the box.
The visitors pressure continued as Sam Hird rifled a shot at goal that was well blocked by Elliott sending the ball out of play for a throw in.
McGlashan, however, persisted in causing the Spireites left back trouble. He earned a free kick on the right wing after being hauled down by Nathan Smith. Moments later, the winger again ran at Smith, his cross into the box was deflected behind the goal. The resulting corner fell to Jason Taylor on the edge of the box who rocketed a right footed volley marginally over the cross bar.
Chesterfields's best chance fell to their veteran steiker. Jack Lester received the ball with his back to goal, wrestling with Elliott he broke free and managed to fire a left footed shot just wide of Scott Brown's right post.
The game looked as though it was close to fizzling out as neither side were able to create any meaningful opportunities.
But the deadlock was broken in the 91st minute. The ball travelled the width of the pitch and Jones received it in plenty of space on the left wing. He had time to place his cross back across the field into the six yard box. A precision delivery that was greeted by the head of on-loan striker Paul Benson who cushioned the ball past a diving Tommy Lee.
Full Time: Cheltenham Town 1-0 Chesterfield
Cheltenham Town FC (4-2-3-1): Brown (GK); Lowe, Hector, Elliott, Jones; Pack, Taylor; Penn (c) (McGlashan '65), Deering (Mohamed '85), Carter (Harrison '65); Benson
Subs not used: Roberts (GK), Jombati, McGlashan, Harrad, Harrison, Duffy
Chesterfield FC (4-4-2): Lee; Talbot, Trotman, Cooper, Smith; O'Shea, Hird (c), Togwell, Townsend; Richards (Lester '62), Gnanduillet (Darokwa '81).
Subs not used: Whitaker, Brindley, Randall, Barrington (GK), Clark.
Referee: Mr. Andy Woolmer
Attendance: 2,195 (125 away supporters)
Robins' Star Man: Sam Deering