Chesterfield fell to a 1-0 defeat as a single strike from Adam Armstrong decided the game at the Ricoh Arena in Coventry City's favour.After dominating the first period, Coventry scored through on-loan striker Armstrong five minutes in the second period when he swivelled and finished in the box.
Chances fell for both sides after that, but after substitute Mani Dieseruvwe received a second yellow card for a handball late on the chances of a leveller decreased and the Sky Blues claimed the points.
There is little recent history between the Spireites and the Sky Blues, neither side could find the net last season in the same fixture and Chesterfield have to go back to 1949 for their last victory in the West Midlands city.
Chesterfield made four changes to the starting eleven against Colchester. Out went Banks, Raglan, Ariyibi and Talbot (suspended) and in came Herd, Hird, Ebanks-Blake and O'Neil.
It was a slow start with neither side grabbing the early initiative, although the home side maintained the lion's share of possession without showing how to get through a resolute Spireites' defence.
The first shot that forced Tommy Lee into any sort of action came in the 15th minute when Jacob Murphy tried his luck from a tight angle, inside the area, and Lee grabbed easily low down.
Striker Armstrong, on loan from Newcastle United, continued to look lively for the home side and fired across goal after 21 minutes with no takers from his team mates. He then missed a peach of a chance in the 27th minute when he cut inside inside the area but fired high and wide.
Moments later Jim O'Brien was the culprit as he fired similarly waywardly from an even more acute angle. From a promising Spireites attack play changed quickly and saw Murphy fire recklessly over.
It was end-to-end stuff as Dan Gardner tested the home keeper with a 30-yard blast and seconds later Ian Evatt headed away for another home flag kick.
With five minutes to the interval Gardner, who had been struggling in training during the week, was substituted by Gboly Ariyibi and prompted an immediate burst of pressure from the Spireites with O'Neil finally firing over.
Romain Vincelot worried the travelling Spireites as he hit over in additional time but it ended all level at the interval.
Mani Dieseruvwe started the second period at the expense of Lee Novak and took up a position on the left.
Coventry went ahead in the 50th minute when Armstrong received a couple of yards inside the box, turned and fired home, on the floor, to Lee's left.
Immediately City burst into life amd moments later Kent fired wide from a great ball from John Fleck.
The Spireites were thwarted on the hour mark when a poor Morsy freekick hit the wall and reached Ebanks-Blake who poked home - unfortunately from an offside position.
Seven minutes later Dieseruvwe went close for the Spireites as his on target shot was turned away by the home keeper, Lee Burge.
A Dan Jones free kick from the right eluded players from both sides and forced Burge to tip away for another Spireites' corner.
At the other end a break set up Murphy who fired wide of the right upright. City continued to press and went close in quick succession - Reda Johnson heading wide of the right post and substitute Marc Antoine-Fortune hitting wide of the same woodwork.
With less than three minutes to go Mani Dieseruvwe was shown his second red card of the season - this time for a second yellow after a deliberate hand ball in the area that warranted the punishment.
City substituted their goal scorer late on but the Spireites failed to take advantage. Ryan Kent was correctly judged offside as he poked home and City saw out the three additional three minutes comfortably.
Coventry City: Burge (gk) - Stokes, Vincelot, Johnson, Fleck, Armstrong (Lameiras 84'), O'Brien (Antoine-Fortune 75'), Ricketts (c), Martin, Murphy, Kent
Subs not used: Charles-Cook (gk), Thomas, Morris, Phillips, Tudgay
Chesterfield: Lee (gk) - Jones, Evatt, Hird, Herd (Banks 79') - Morsy (c), O'Neil, Novak (Dieseruvwe 46'), O'Shea, Gardner (Ariyibi 40') - Ebanks-Blake
Subs not used: Cairns (gk), Raglan, Gnanduillet, Humphreys
Coventry City: Armstrong 50'