THE worst away run of Peter Jackson's managerial career has left nine-man Town looking anxiously over their shoulders.
A controversial seventh straight away defeat to a penalty double by Shane Nicholson places them eight points above the drop zone but, on form, only Oldham have a worse recent record in League I.
That means the pressure is on now to beat bottom club Stockport at the Galpharm on Saturday, with Town needing at least a couple of wins to ensure they steer clear of potential problems.
Including the Edgeley Park side, Town have still to play three of the clubs below them in the table, so their fate is very much in their own hands.
It doesn't help, however, that Jackson will be forced into more changes because of suspensions for dismissed duo Tom Clarke and Efe Sodje to add to that of Jon Worthington this coming weekend.
Town are also making life hard for themselves by missing significant chances to take control of games.
On Saturday, Chris Brandon was clean through after 72 seconds only to fire straight at the keeper, while Andy Booth hit the bar with a header and fired another great opportunity over the top.
Those misses came back to haunt them.
While Town could have no compaints about the award of either penalty, the 17-year-old Clarke was unlucky to see red when conceding the first for a tug on Jamie McMaster in the 52nd minute.
Leicester referee Brian Curson decided he was the last man and, in denying a goalscoring opportunity, had to go - thus becoming the youngest red-card victim in Town history.
But Tony Carss booted clear and David Mirfin was also covering.
With Nicholson blasting the ball low to Paul Rachubka's right - it was their first shot on target and one of only three in the entire game - Town were up against it, and the task became a whole lot harder when Mirfin brought down McMaster with 13 minutes left for Nicholson's second spot-kick.
Mirfin atoned only two minutes later with a neat back header from Nathan Clarke's raking free-kick, but there was to be no last-gasp escape.
In fact, Town played out the final minute of normal time and five minutes of added with only nine players following the third dismissal of the season for Sodje, who mistimed a challenge on Gareth Davies to earn his second yellow card for a trip from behind when falling.
It came only moments after a full-scale flare-up between the sides - caused largely by growing frustration at some of the refereeing decisions - and which resulted in bookings for both Nicholson and Town's Brandon, who took a lot of stick from fans on his first return to Saltergate.
It was a shame he didn't silence them in the second minute of the match when the hard-working Adnan Ahmed put him clean through.
He tried to take the shot early and catch out loan keeper Marton Fulop from Tottenham, who was making his League debut, but he planted a tame effort within easy reach for the lanky Hungarian Under 21 international.
The outstanding Nathan Clarke caused Chesterfield all sorts of problems with his long throw-ins and Booth had already nodded one straight at the keeper by the time he hit the bar from another with only 11 minutes on the clock and with Town in complete control.
Referee Curson missed what appeared a clear push on Booth in the box in the 21st minute (there were also loud appeals for a similar incident in the second half), while Chesterfield looked more comfortable when Wayne Allison settled in as replacement for the injured Mark Hudson.
Even then, a quick throw by Delroy Facey should have presented Booth with a goal on 37 minutes, but the big striker fired over from the angle and it meant Chesterfield, who had seen Alan O'Hare miss an open goal from Derek Niven's break, were able to make the most of their second-half chances.
They were eventually able to celebrate a first home win since November as Town, who forced a couple of late chances for Tony Carss in a frantic finale, had to acknowledge another bitter disappointment for their 1,200 travelling fans.
Man of the Match: Nathan Clarke
GETS better by the game and certainly looked the part as captain, driving the team onwards. He found it tough in the air against Allison, but his tackling was just superb.
HOW THEY RATED:
Paul Rachubka While Alan O'Hare missed an open goal, he was tested by only one shot on target apart from the penalties Rating: 7/10
Andy Holdsworth Put in a couple of decent crosses in the first half as he pushed forward well. Taken off as Town fielded a third striker in Abbott Rating: 6/10
Tom Clarke Had a tough time as Niven and McMaster attacked down his wing but did not deserve his red card for the penalty Rating: 6/10
David Mirfin Centre-back, left-back and goalscorer all in the same day. Oh, and he conceded the second penalty to boot. Rating: 7/10
Nathan Clarke Led by example in his first game as skipper with some tremendous tackling and sensible reading of the game Rating: 8/10
Michael Collins Played more of an anchoring role first half. Sacrificed in the second for Efe Sodje after Clarke's sending-off Rating: 6/10
Tony Carss Involved a lot as Town started well and, in added time, had a couple of chances to maybe snatch a point Rating: 6/10
Adnan Ahmed No-one covered more ground on the day. He worked superbly and created a clear early chance for Brandon Rating: 7/10
Chris Brandon Missed a clear chance in the second minute but worked hard. Given stick all through by the Chesterfield fans Rating: 7/10
Andy Booth Hit the bar and fired another chance over. Terrific first half, grafted through the second and close to top-man marks Rating: 7/10
Delroy Facey Battled for headers and used his pace at times but couldn't get onto the end of anything like a decent chance Rating: 6/10
SPOTLIGHT ON THE REF: Brian Curson from Leicester managed to infuriate both sets of players with his picky decisions and it was no surprise, three minutes from time, when tempers boiled over following an altercation between Chris Brandon and the penalty scorer Shane Nicholson.
There were seven yellow cards altogether and two reds (for Tom Clarke and Efe Sodje) and yet the game didn't really feature a nasty challenge. The officials also missed what appeared straightforward pushes on Andy Booth in the Chesterfield box.
Chesterfield: Fulop; Bailey, Nicholson, Blatherwick, Evatt; Allott, Hudson (Allison 15), Niven, O'Hare; DeBolla (Davies 87), McMaster. Subs not used: Richmond, Fowler, Logan.